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

HRID 2353085노트

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HRID 2353085 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
100 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a1b5ac102b614d878cdc120e7801dc7f
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749997B2

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