Diazomethane → 4-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid, methyl ester

HRID 248078Notes

Reaction equation

HRID 248078 reaction equation
[CH3:1][C:2]([CH3:21])([O:4][C:5](=[O:20])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:10][CH:9]=1)[CH3:3].[N+](=[CH2:24])=[N-]>C(OCC)C>[CH3:3][C:2]([CH3:1])([O:4][C:5](=[O:20])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH:15]([CH3:19])[C:16]([O:18][CH3:24])=[O:17])=[CH:10][CH:9]=1)[CH3:21]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 197645314-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid

Product 1

HCID 867467874-[[2-(1,1-Dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dissolve (+)-4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid (90% ee) (6.04 g, 20.5 mmol) in ethyl ether (400 mL) and treat with excess diazomethane. Wash with saturated sodium hydrogen carbonate (2×300 mL) and brine (300 mL). Dry (MgSO4) and evaporate the solvent in vacuo to give (+)-4-[[2-(1,1-dimethylethoxy)-2-oxoethyl]oxy]-alpha-methyl-benzenepropanoic acid, methyl ester (5.85 g).

Workup

  1. washWash with saturated sodium hydrogen carbonate (2×300 mL) and brine (300 mL)
  2. dry with materialDry (MgSO4)
  3. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-cb03b59edc6f49b58f2d6387d49e8bb5
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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