Sodium borohydride → HCID 57739004, compound

HRID 1745898Notes

Reaction equation

HRID 1745898 reaction equation
[F:1][C:2]([O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1)=[C:3]([F:5])[F:4].[BH4-].[Na+]>C1C=CC=CC=1.C(O)C>[F:1][C:2]([O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1)=[C:3]([F:5])[F:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22227324HCID 22227324, compound

Product 1

HCID 57739004HCID 57739004, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21965192Npc112006Solvent

Procedure

To a solution of 4-(trifluorovinyloxy)benzaldehyde (about 35 mmol) in benzene/ethanol (75/75 mL) at room temperature was added sodium borohydride (1.8 g, 1.3 eq). The resulting mixture was stirred at room temperature for 3 h. Under reduced pressure, all the solvent was evaporated. The residue was extracted by CH2Cl2 for 1 h and dried over sodium sulfate. The product was purified by chromatography using CH2Cl2 as the eluent to afford 4-(trifluorovinyloxy)benzyl alcohol as colorless oil (5.0 g, yield 68%). 1H NMR (CDCl3): δ 7.36 (d, J=8.8 Hz, 2H), 7.09 (d, J=8.8 Hz, 2H), 4.67 (s, 2H), 2.03 (s, 1H).

Workup

  1. customUnder reduced pressure, all the solvent was evaporated
  2. extractionThe residue was extracted by CH2Cl2 for 1 h
  3. dry with materialdried over sodium sulfate
  4. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-11da16b25528478d88b02af9d5a4bac5
Source dataset
uspto-grants-2006_03
Patent number
US07019453B2

Reaction notes

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