Sodium borohydride → HCID 66603245, compound

HRID 604181Notes

Reaction equation

HRID 604181 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH3:23])=[C:8]([C:10]2[C:11]([CH:20]=[O:21])=[CH:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=2)[CH:9]=1)([CH3:3])=[CH2:2].[BH4-].[Na+]>O1CCCC1.C(O)C.C(Cl)Cl>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:22][CH3:23])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][C:11]=2[CH2:20][OH:21])[CH:9]=1)([CH3:3])=[CH2:2]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 86626912HCID 86626912, compound

Product 1

HCID 66603245HCID 66603245, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

5′-Isopropenyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-carbaldehyde (5.0 g) is dissolved in a mixed solvent of tetrahydrofuran (100 ml), ethanol (30 ml) and methylene chloride (10 ml), and thereto is added sodium borohydride (646 mg) and the mixture is stirred at room temperature for 10 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=49:1→4:1) to give (5′-isopropenyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-yl)-methanol (4.73 g). MS (m/z): 307 [M+H]+

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=49:1→4:1)

Sources & evidence

ORD record
ord-24723cdb2ad8432bbffb392fed198f84
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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