(Trifluoromethyl)trimethylsilane → 2-(6-Bromo-2-naphthyl)-1,1,1-trifluoropropan-2-ol

HRID 1094651

反応式

HRID 1094651 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](=[O:14])[CH3:13])[CH:6]=[CH:5]2.C[Si]([C:19]([F:22])([F:21])[F:20])(C)C.CO.Cl>C([O-])(=O)C.[Li+].CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])([CH3:13])[C:19]([F:22])([F:21])[F:20])[CH:6]=[CH:5]2

参加物

6

反応物 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 124330821-(6-Bromonaphthalen-2-yl)ethanoneHCID 21893726Hydrochloride methanol

生成物 1

HCID 666376052-(6-Bromo-2-naphthyl)-1,1,1-trifluoropropan-2-ol収率 79.3%

試薬・触媒・溶媒 2

HCID 3474584Lithium acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

To a DMF (25 ml) solution of 1-(6-bromo-2-naphthyl)ethanone (1230 mg, 4.94 mmol), trimethylsilyl trifluoromethane (1050 mg, 7.41 mmol) and lithium acetate (16.3 mg, 0.247 mmol) were added and the mixture was stirred for 12 hours at room temperature. Then, the reaction was quenched with ethyl acetate and water, then the organic layer was separated and dried over sodium sulfate. The solvent was evaporated to give the residue which was treated with methanol-hydrogen chloride to give the product (1.25 g, 63%) as colorless oil. 1H NMR (300 MHz, CDCl3) δ ppm 1.88 (3H, s), 7.57-7.60 (1H, m), 7.68-7.81 (3H, m), 8.02-8.05 (2H, m).

後処理

  1. customThen, the reaction was quenched with ethyl acetate and water
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customto give the residue which

出典と根拠

ORDレコード
ord-09b33e7513b64cddae994c4dd7595c3b
出典データセット
uspto-grants-2012_03
特許番号
US08134004B2

関連ノート

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