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 Synthesis

56-86-0
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$5.00/25g

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

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]