ChemicalBook CAS DataBase List (R)-(-)-2-Methoxypropanol

(R)-(-)-2-Methoxypropanol synthesis

6synthesis methods

Product Name:(R)-(-)-2-Methoxypropanol
CAS Number:6131-59-5
Molecular formula:C4H10O2
Molecular Weight:90.12

23943-96-6

6131-59-5

General procedure for the synthesis of (R)-2-methoxy-1-propanol from (R)-2-methoxypropionic acid:[1239] 858 μL (8.39 mmol, 1.8 eq.) of borane/dimethyl sulfide complex was slowly added to a solution containing 500 mg (4.66 mmol) of (R)-(+)-2-methoxypropionic acid under argon protection and at 0 °C. The reaction mixture was stirred overnight at room temperature and then 2M aqueous sodium hydroxide solution was added dropwise. After completion of the reaction, phase separation was carried out and the aqueous phase was extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered, concentrated under reduced pressure (water bath temperature controlled at 300 mbar) and finally dried to give the product. Yield: 490 mg (quantitative). [1240] 1H-NMR (400 MHz, DMSO-d6): δ [ppm] = 4.55 (t, 1H), 3.40-3.31 (m, 1H), 3.30-3.20 (m, 2H), 3.24 (s, 3H), 1.02 (d, 3H).

23943-96-6 Synthesis

23943-96-6
83 suppliers
$52.00/100mg

6131-59-5
42 suppliers
$503.87/5MG

Yield: 100%

Reaction Conditions:

with dimethylsulfide borane complex in dichloromethane at 0 - 20;Inert atmosphere;

Steps:

29.1A (2R)-2-Methoxypropan-1-ol
[1239] Under argon and at oo C., 858 fll (8.39 mmol, 1.8eq.) ofborane/dimethyl sulphide complex were added dropwiseto a solution of 500 mg ( 4.66 mmol) of (R)-( + )-2-methoxypropionic acid in 10 ml of dichloromethane, thereaction mixture was stirred at RT overnight and aqueoussodium hydroxide solution (2M) was then added dropwise.After phase separation, the aqueous phase was extracted withdichloromethane. The combined organic phases were dried(sodium sulphate), filtered, concentrated under reduced pressure(water bath 300 mbar) and dried.Yield: 490 mg (quant.)[1240] 1H-NMR (400 MHz, DMSO-d6): o [ppm]=4.55 (t,lH), 3.40-3.31 (m, lH), 3.30-3.20 (m, 2H), 3.24 (s, 3H), 1.02(d, 3H).

References:

BAYER PHARMA AKTIENGESELLSCHAFT;RÖHRIG, Susanne;HILLISCH, Alexander;STRAßBURGER, Julia;HEITMEIER, Stefan;SCHMIDT, Martina Victoria;SCHLEMMER, Karl-Heinz;TERSTEEGEN, Adrian;BUCHMÜLLER, Anja;GERDES, Christoph;SCHÄFER, Martina;KINZEL, Tom;TELLER, Henrik;SCHIROK, Hartmut;KLAR, Jürgen;NUNEZ, Eloisa JIMENEZ US2016/52884, 2016, A1 Location in patent:Paragraph 1238-1240

40105-20-2 Synthesis