Sodium borohydride → 2-(4-Fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl alcohol

HRID 1584721노트

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HRID 1584721 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:9]=2[CH:10]=[O:11])=[CH:4][C:3]=1[CH3:18].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:9]=2[CH2:10][OH:11])=[CH:4][C:3]=1[CH3:18]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 133169792-(4-Fluoro-3-methyl-phenyl)-4,6-dimethylbenzaldehyde

생성물 1

HCID 133169802-(4-Fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl alcohol수율 98.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2.90 grams (12 mmol) of 2-(4-fluoro-3-methyl-phenyl)-4,6-dimethylbenzaldehyde (prepared according to Stokker, Journ. Med. Chem., Vol. 29 p.170, 1986) was reduced with 0.454 grams (12 mmol) of sodium borohydride in ethanol (20 mL) at 0° C. The reaction was stirred 1 hr, quenched with aqueous ammonium chloride and the mixture extracted with ether. The organic portion was dried (MgSO4) and concentrated to give 2.90 grams of 2-(4-fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl alcohol as an oil which solidified on standing. The crude solid was treated with 1.31 mL of thionyl chloride and heated on a steam bath for 1 hour. After cooling to room temperature, the crude mixture was taken up in water and extracted with ether. The ether was washed with water and dried(MgSO4), and concentrated to give an oily residue which was purified by silica gel chromatography (25% methylene chloride/75% hexane) to give 2.70 grams (85.6%) of 2-(4-fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl chloride as a solid. 2.06 grams (7.84 mmol) of 2-(4-fluoro-3-methyl-phenyl)-4,6-dimethylbenzyl chloride was treated with ethyldiphenylphosphinite (2.08 grams, 9.01 mmol) and heated to 150° C. for 3 hrs. After cooling to room temperature, the crude mixture was purified by silicagel chromatography (10% acetone/90% methylene chloride) and the appropriate fractions concentrated and recrystallized from ether/hexane to provide the above-titled compound. MP 109-111° C.

후처리

  1. customquenched with aqueous ammonium chloride
  2. extractionthe mixture extracted with ether
  3. dry with materialThe organic portion was dried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0696c4f5c3cc45d89c561b5ecddb56b6
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05935945

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