Sodium borohydride → HCID 66602942, compound

HRID 604178Notes

Reaction equation

HRID 604178 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:24][CH3:25])=[C:8]([C:10]2[C:11]([CH:22]=[O:23])=[CH:12][C:13]([C:18]([F:21])([F:20])[F:19])=[C:14]([O:16][CH3:17])[CH:15]=2)[CH:9]=1)([CH3:3])[CH3:2].[BH4-].[Na+]>O1CCCC1.C(O)C.C(Cl)Cl>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:24][CH3:25])=[C:8]([C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([C:18]([F:21])([F:19])[F:20])=[CH:12][C:11]=2[CH2:22][OH:23])[CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 86626909HCID 86626909, compound

Product 1

HCID 66602942HCID 66602942, compoundYield 81.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5′-Isopropyl-5,2′-dimethoxy-4-trifluoromethyl-biphenyl-2-carbaldehyde (692 mg) is dissolved in a mixed solvent of tetrahydrofuran (12 ml), ethanol (3.5 ml) and methylene chloride (1 ml), and thereto is added sodium borohydride (82 mg) and the mixture is stirred at room temperature for 40 minutes. The reaction solution is concentrated under reduced pressure and thereto are added ethyl acetate and water, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1) to give (5′-isopropyl-5,2′-dimethoxy-4-trifluoromethyl-biphenyl-2-yl)-methanol (566 mg). MS (m/z): 337 [M+H—H2O]+

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionare added ethyl acetate and water
  3. customthe mixture is separated
  4. washthe organic layer is washed with a saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1)

Sources & evidence

ORD record
ord-60db70cca00946a1a78791d58837e58c
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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