Methanol → HCID 58127012, compound

HRID 1971850Notes

Reaction equation

HRID 1971850 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[S:13][CH3:14].CC(C[AlH]CC(C)C)C.CO>C1(C)C=CC=CC=1.CC(=O)OCC>[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH:3]=[O:2])=[C:7]([S:13][CH3:14])[CH:8]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 58126901HCID 58126901, compound

Product 1

HCID 58127012HCID 58127012, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(4-fluoro-2-methylsulfanyl-phenyl)-propionic acid methyl ester (1 g, 4.3 mmol) in dry toluene was added DIBAL-H (5.2 ml in toluene, 1N) drop-wise at −78° C. After stirring at this temperature for 1 h, methanol (5 ml) was added dropwise to quench the reaction. The mixture was warmed to room temperature and diluted with EA. The mixture was washed with brine, dried and concentrated. The residue was purified by column chromatography to give the titled compound (804 mg, yield 92%)

Workup

  1. customto quench
  2. customthe reaction
  3. washThe mixture was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-10fae4589f5f49709fe9c5d29d9fe3a8
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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