Tetrahydrofuran → 4-(2-Vinyl-benzooxazol-5-yl)-benzonitrile

HRID 424949

反応式

HRID 424949 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]=[CH2:11])=[N:7][C:6]=2[CH:12]=1.[C:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)#[N:14].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.O1CCCC1>CCCCCC>[CH:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([C:18]3[CH:19]=[CH:20][C:15]([C:13]#[N:14])=[CH:16][CH:17]=3)=[CH:12][C:6]=2[N:7]=1)=[CH2:11]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 27343264-Cyanophenylboronic acidHCID 219800995-Bromo-2-ethenyl-1,3-benzoxazole

生成物 1

HCID 219800914-(2-Vinyl-benzooxazol-5-yl)-benzonitrile収率 78%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
23 °C

実験手順

A mixture of 224 mg (1 mmol) of 5-bromo-2-vinyl-benzooxazole, 191 mg (1.3 mmol) of 4-cyanophenylboronic acid, 55 mg (0.03 mmol) of tris-(dibenzylidineacetone)dipalladium (0) (CAS #52409-22-0), 0.2 mL (0.06 mmol) of a 10% solution of tri-tert-butylphosphine in hexane, and 1.5 mL of tetrahydrofuran was stirred at 23° C. for 24 hours. It was then heated at 65° C. for 0.5 hour, then cooled. The mixture was suction filtered to remove particulates, then partitioned between 80 mL of water and a mixture of 30 mL of ethyl acetate and 10 mL of hexane. The organic phase was collected, dried over Na2SO4, and purified by flash chromatography on silica gel (eluting with 1:1 hexane: dichloromethane) to give 4-(2-vinyl-benzooxazol-5-yl)-benzonitrile (192 mg, 78%) as a white solid: mp 143-144° C.;

後処理

  1. temperatureIt was then heated at 65° C. for 0.5 hour
  2. temperaturecooled
  3. filtrationfiltered
  4. customto remove particulates
  5. custompartitioned between 80 mL of water
  6. additiona mixture of 30 mL of ethyl acetate and 10 mL of hexane
  7. customThe organic phase was collected
  8. dry with materialdried over Na2SO4
  9. custompurified by flash chromatography on silica gel (eluting with 1:1 hexane: dichloromethane)

出典と根拠

ORDレコード
ord-fdee3ae3e70641eda44083ba7aa8aeb1
出典データセット
uspto-grants-2012_01
特許番号
US08106088B2

関連ノート

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