Methanol → (R)-Methyl 2-hydroxy-3-methylbutanoate

HRID 2043143노트

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HRID 2043143 반응식
[OH:1][C@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].[CH3:9]O>CCCCCC>[OH:1][C@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([O:5][CH3:9])=[O:4]

참가 물질

4

반응물 2

HCID 887MethanolHCID 5289545(-)-2-Hydroxy-3-methylbutyric acid

생성물 1

HCID 10887945(R)-Methyl 2-hydroxy-3-methylbutanoate수율 30%

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
0 °C

실험 절차

To a solution of (R)-2-hydroxy-3-methylbutanoic acid (5.0 gm, 42.2 mmol) in methanol was added a solution of TMS.CH2N2 (2M) in hexane (65 mL), at 0° C., over 20 min. The reaction mixture was stirred at 0° C. for 1 h. The reaction was concentrated with a bath temperature of 20° C. and vacuum greater than 50 mm Hg. Purification via silica gel chromatography using 2-100% EtOAc in hexanes gave the ester as a yellow oil (438 mg, 12.7 mmol, 30% yield). 1H NMR (400 MHz, DMSO-d6) δ 5.30 (d, J=5.1 Hz, 1H), 3.81 (t, J=0.8 Hz, 1H), 3.63 (s, 3H), 1.94-1.86 (m, 1H), 0.88-0.82 (m, 6H).

후처리

  1. concentrationThe reaction was concentrated with a bath temperature of 20° C. and vacuum greater than 50 mm Hg
  2. customPurification via silica gel chromatography

출처 및 근거

ORD 기록
ord-0ce73edfb4484dafad313ba59d486485
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586589B2

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