Water → (4-Phenylbicyclo[2.2.2]oct-1-yl)acetonitrile

HRID 908128ノート

反応式

HRID 908128 の反応式
C1(C)C=CC(S(O[CH2:11][C:12]23[CH2:19][CH2:18][C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)([CH2:16][CH2:17]2)[CH2:14][CH2:13]3)(=O)=O)=CC=1.[C-:27]#[N:28].[Na+].O>CS(C)=O>[C:20]1([C:15]23[CH2:18][CH2:19][C:12]([CH2:11][C:27]#[N:28])([CH2:17][CH2:16]2)[CH2:13][CH2:14]3)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 962WaterHCID 8929Sodium CyanideHCID 866252464-Phenylbicyclo[2.2.2]oct-1-ylmethyl toluene-4-sulfonate

生成物 1

HCID 67414049(4-Phenylbicyclo[2.2.2]oct-1-yl)acetonitrile収率 93%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

A stirred mixture of 4-phenylbicyclo[2.2.2]oct-1-ylmethyl toluene-4-sulfonate (2.5 g, 6.75 mmol) and sodium cyanide (0.5 g, 10.20 mmol) in DMSO (20 mL) was heated at 100° C. under nitrogen for 5 h. After cooling overnight the mixture was poured into water (100 mL) then extracted with DCM (2×100 mL) then methyl t-butyl ether (3×100 mL). The DCM and methyl t-butyl ether phases were separately combined, washed with water (50 mL) and dried (MgSO4). The organic phases were then combined and the solvents evaporated to give the crude product which was purified by silica column chromatography (silica 40-63 micron) eluting with hexane:ethyl acetate 19:1 to give the title compound as a white solid (1.4 g; 93%).

後処理

  1. temperatureAfter cooling overnight the mixture
  2. extractionthen extracted with DCM (2×100 mL)
  3. washwashed with water (50 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvents evaporated
  6. customto give the crude product which
  7. customwas purified by silica column chromatography (silica 40-63 micron)
  8. washeluting with hexane:ethyl acetate 19:1

出典と根拠

ORDレコード
ord-3aa235caef6c4e2b91ffd27c9033d432
出典データセット
uspto-grants-2011_09
特許番号
US08017603B2

反応ノート

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