Sodium borohydride → Tert-butyl 3-(4-((2'-(hydroxymethyl)biphenyl-3-yl)methoxy)phenyl)propanoate

HRID 2422306Notes

Reaction equation

HRID 2422306 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:19][CH:18]=2)[CH:10]=1)=[O:2].[BH4-].[Na+]>CO.O1CCCC1>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:21][CH:22]=2)[CH:10]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 23082902HCID 23082902, compound

Product 1

HCID 23082953Tert-butyl 3-(4-((2'-(hydroxymethyl)biphenyl-3-yl)methoxy)phenyl)propanoateYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 3-(4-(2′-formylbiphenyl-3-ylmethoxy)phenyl)propanoate (0.30 g, 0.72 mmol) was dissolved in a mixed solution of methanol (6 mL) and tetrahydrofuran (6 mL), and sodium borohydride (14 mg, 0.36 mmol) was added under ice-cooling, and the mixture was stirred at the same temperature for 2 hrs. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate, washed with 1N hydrochloric acid and saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-1/1) to give the title compound (0.25 g, yield 83%) as a colorless oil.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with 1N hydrochloric acid and saturated brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-1/1)

Sources & evidence

ORD record
ord-826d0074c7cd46fab6c3342b40a67b53
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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