ChemicalBook CAS DataBase List (S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID

(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID synthesis

6synthesis methods

Product Name:(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
CAS Number:21461-84-7
Molecular formula:C5H6O4
Molecular Weight:130.1

56-86-0

(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID

21461-84-7

General procedure for the synthesis of (S)-5-oxo-2-tetrahydrofuran carboxylic acid from L-glutamic acid: L-glutamic acid (10.07 g, 0.068 mol, JK CHEMICA) was dissolved in 20 mL of water in a conical flask. A solution of NaNO2 (7.0 g, 0.102 mol, Shantou Xilong Chemical Factory) in 20 mL of water was slowly added to this solution at -5°C, along with HCl and 40 mL of water. The reaction mixture was stirred continuously at room temperature for 12 hours. Subsequently, the reaction mixture was subjected to vacuum evaporation at less than 50 °C to obtain a yellow oily substance. This oily substance was dissolved in EtOAc, filtered to remove the solid formed and the solid was washed with EtOAc. The filtrate and washings were combined and dried with Na2SO4. Finally, the solvent was removed by vacuum concentration to afford (S)-5-oxo-2-tetrahydrofuran carboxylic acid as a light yellow oil (8.1 g, 91.6% yield). The product was analyzed by mass spectrometry (ESI, cation mode), m/z: 130.9 (M+1); 1H NMR (400 MHz, CDCl3) data were as follows: δ 2.27-2.41 (m, 1H), 2.44-2.65 (m, 3H), 5.09 (m, 1H), 9.12-9.55 (m, 1H).

56-86-0 Synthesis

56-86-0
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$5.00/25g

21461-84-7
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$19.00/250mg

Yield:21461-84-7 98%

Reaction Conditions:

with hydrogenchloride;sodium nitrite in water at 0 - 20;

Steps:

3.1. (S)-5-Oxotetrahydrofuran-2-carboxylic acid (6)

To the suspension of L-glutamic acid (10.0 g, 68 mmol) and NaNO2 (7.5 g, 108.7 mmol, 1.6 equiv) in water (100 mL) was added HCl (10 mL concentrated diluted to 50 mL) dropwise via an addition funnel at 0° C with vigorous stirringfor 1 h. The mixture was warmed to rt and stirred for 18 h. The water was evaporated and then EtOAc (200 mL) wasadded. The mixture was stirred for 30 min and filtered. The solid cake was washed with EtOAc (2 x 75 mL). The organic extracts were combined and dried over MgSO4. The solventwas evaporated in vacuo and the residue was left under high vacuum for 12 h to give the lactone acid 6 (8.67 g, 98% yield) as a solid syrup. 1H NMR (500 MHz, CDCl3) δ 5.01-4.97 (m, 1H), 2.68-2.53 (m, 3H), 2.44-2.35 (m, 1H). NMR spectroscopic data matched with the published data [12].

References:

Xuan, Duc Dau [Letters in Organic Chemistry,2021,vol. 18,# 1,p. 58 - 65]