Ethyl Acetate → (4-Benzyloxy-5'-isopropyl-2'-methoxy-biphenyl-2-yl)-methanol

HRID 604189Notes

Reaction equation

HRID 604189 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:26]=[O:27])[C:12]([C:15]2[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[CH:17][C:16]=2[O:24][CH3:25])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([CH:21]([CH3:22])[CH3:23])[CH:18]=[CH:17][C:16]=2[O:24][CH3:25])=[C:11]([CH2:26][OH:27])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 866269194-Benzyloxy-5'-isopropyl-2'-methoxy-biphenyl-2-carbaldehyde

Product 1

HCID 67087233(4-Benzyloxy-5'-isopropyl-2'-methoxy-biphenyl-2-yl)-methanolYield 108%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-2-carbaldehyde (1.16 g) is dissolved in ethanol (15 ml) and thereto is added sodium borohydride (122 mg) and the mixture is stirred at room temperature for 10 minutes. Thereto are added a saturated aqueous ammonium chloride solution and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give (4-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-2-yl)-methanol (1.26 g). MS (m/z): 345

Workup

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12a5013d06f84f19a62d4febc8ff8916
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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