Sodium borohydride → (2'-Hydroxymethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

HRID 38685Notes

Reaction equation

HRID 38685 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH:24]=[O:25])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][C:15]=2[CH2:24][OH:25])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86633171(2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Product 1

HCID 67431174(2'-Hydroxymethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (2′-formyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.844 g, 2.30 mmol) in MeOH was added sodium borohydride (0.096 g, 2.53 mmol), and the reaction was stirred at room temperature for 15 minutes. The mixture was concentrated, and the residue was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between EtOAc and H2O
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b42e430b52dd4fcbb22ed453d0a0b178
Source dataset
uspto-grants-2013_09
Patent number
US08524748B2

Reaction notes

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