Sodium borohydride → HCID 11230594, compound

HRID 525429Notes

Reaction equation

HRID 525429 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]=1)=[O:4].[BH4-].[Na+]>C(Cl)Cl>[F:1][C:2]([F:17])([F:18])[CH:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]=1)[OH:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 24726833HCID 24726833, compound

Product 1

HCID 11230594HCID 11230594, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,2,2-trifluoro-1-(6-methoxynaphthalen-2-yl)ethanone (1 g, 3.9 mmol) and NaBH4 (312 mg, 7.8 mmol, 2 eq) in DCM (20 mL) was stirred at room temperature for 5 h. The reaction mixture was quenched with water (5 mL), washed with brine (10 mL*2), dried over Na2SO4 and concentrated to give 2,2,2-trifluoro-1-(6-methoxynaphthalen-2-yl)ethanol (800 mg, yield: 80%) as a white solid. ESI-MS (M+1)+: 255.1. 1HNMR (400 MHz, CDCl3) δ: 7.80 (s, 1H), 7.72-7.68 (m, 2H), 7.46 (d, J=8.4 Hz, 1H), 7.13-7.07 (m, 2H), 5.09 (q, J=6.4 Hz, 1H), 3.85 (s, 3H).

Workup

  1. customThe reaction mixture was quenched with water (5 mL)
  2. washwashed with brine (10 mL*2)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-65047c0551bc4b74aed87c65d4a9c2fb
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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