Phenol → 1-Benzhydryl-3-phenoxyazetidine

HRID 72399

反応式

HRID 72399 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].CS(O[CH:15]1[CH2:18][N:17]([CH:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16]1)(=O)=O>C1(C)C=CC=CC=1>[CH:19]([N:17]1[CH2:18][CH:15]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:16]1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

5

反応物 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

生成物 1

HCID 28175781-Benzhydryl-3-phenoxyazetidine収率 40%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
60 °C

実験手順

Phenol (2.2 g, 23.4 mmol) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 937 mg, 23.4 mmol) in toluene (40 ml) and the mixture was heated at 60° C. for 2 hours. The temperature was then increased to 80° C. and a solution of 1-benzhydrylazetidin-3-yl methanesulfonate (D19) (4.78 g, 14.6 mmol) in toluene (80 ml) was added dropwise. After stirred at 80° C. for 2 hours, the resulting mixture was cooled to room temperature, then washed with water (100 ml) and brine (100 ml), dried over Na2SO4, filtered and evaporated in vacuo. The crude residue was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate from 30:1 to 20:1. Collected fractions after solvent evaporation were further purified by preparative HPLC to afford the title compound (D20) (1.84 g) as a white solid.

後処理

  1. temperatureThe temperature was then increased to 80° C.
  2. temperaturethe resulting mixture was cooled to room temperature
  3. washwashed with water (100 ml) and brine (100 ml)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude residue was purified by flash chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate from 30:1 to 20:1
  8. customCollected fractions after solvent evaporation
  9. customwere further purified by preparative HPLC

出典と根拠

ORDレコード
ord-bf882239aee74feb95c3fe1051f93979
出典データセット
uspto-grants-2014_09
特許番号
US08828987B2

関連ノート

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