Methanol → (R)-Methyl 2-hydroxy-3-methylbutanoate
Reaction equation
[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]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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), 3.63H), 1.94-1.86 (m, 1H), 0.88-0.82 (m, 6H).
Workup
- concentrationThe reaction was concentrated with a bath temperature of 20° C. and vacuum greater than 50 mm Hg
- customPurification via silica gel chromatography
Sources & evidence
- ORD record
- ord-fadd9cea736c4c0ca34775a587181f98
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07799822B2
Reaction notes
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