Methanol → 4-Methoxy-3-methyl-4-oxobutanoic acid

HRID 226277

Reaction equation

HRID 226277 reaction equation
C[O:2][C:3](=[O:10])[CH2:4][C:5](=[CH2:9])[C:6]([OH:8])=[O:7].[H][H].[CH3:13]O>>[CH3:13][O:8][C:6](=[O:7])[CH:5]([CH3:9])[CH2:4][C:3]([OH:2])=[O:10]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 817914-Methyl hydrogen 2-methylenesuccinateHCID 178418361HCID 178418361, compound

Product 1

HCID 139255704-Methoxy-3-methyl-4-oxobutanoic acid

Procedure

5.73 g (39.8 mmol) of 2-methylenesuccinic acid 4-monomethyl ester were introduced into 12 ml of methanol under protective gas in a 50 ml glass autoclave, and 0.12 ml of a solution of 6.6 mg of (RophosARhCOD)CF3SO3 (=precatalyst) in 3 ml of methanol was added (0.00036 mmol of precatalyst). Hydrogenation was then carried out at 60° C. under 5 bar of hydrogen. Conversion of the precursor was complete after 16 h. The enantiomeric excess of the product was 98%.

Workup

  1. additionwas added (0.00036 mmol of precatalyst)

Sources & evidence

ORD record
ord-70d91d5360de46ea999e021d636b4083
Source dataset
uspto-grants-2009_07
Patent number
US07557240B2

Linked notes

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