Methanol → Ethyl 6-(4-fluoro-1-naphthyl)-5-hydroxy-6-oxohexanoate

HRID 747458

Reaction equation

HRID 747458 reaction equation
Br[CH:2]([C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([F:23])=[CH:15][CH:14]=1)=[O:12])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C([O-])=[O:25].[Na+].CO>C(OCC)(=O)C>[F:23][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([C:11](=[O:12])[CH:2]([OH:25])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2723810Sodium FormateHCID 18174722Ethyl 5-bromo-6-(4-fluoro-1-naphthyl)-6-oxohexanoate

Product 1

HCID 18174704Ethyl 6-(4-fluoro-1-naphthyl)-5-hydroxy-6-oxohexanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 5-bromo-6-(4-fluoro-1-naphthyl)-6-oxohexanoate (34.3 g), sodium formate (34.0 g) and methanol (150 ml) was stirred with heating under reflux for 16 hours. The reaction mixture was diluted with ethyl acetate (500 ml) and washed with water (200 ml×2). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 6-(4-fluoro-1-naphthyl)-5-hydroxy-6-oxohexanoate was obtained as a yellow oil (19.0 g, 65%) from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 16 hours
  3. washwashed with water (200 ml×2)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1e793f0b562b41f9afba3943552c21d5
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Linked notes

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