Ethyl Acetate → HCID 67087250, compound

HRID 604194Notes

Reaction equation

HRID 604194 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][C:10]=1[CH:11]=[O:12])[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:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:13][C:10]=1[CH2:11][OH:12])[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 86626923HCID 86626923, compound

Product 1

HCID 67087250HCID 67087250, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Benzyloxy-5-trifluoromethoxy-benzaldehyde (1.40 g) is dissolved in ethanol (30 ml) and thereto is added sodium borohydride (189 mg) and the mixture is stirred at room temperature for 30 minutes. To the reaction solution are added 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. The residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1) to give (2-benzyloxy-5-trifluoromethoxy-phenyl)methanol (1.10 g).

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
  5. customThe residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-804474e1646240a3b2716869cebdd2d7
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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