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

HRID 900197

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HRID 900197 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
23 °C

실험 절차

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.; 1H NMR (300 MHz, CDCl3) δ 7.90 (d, J=1.8 Hz, 1 H), 7.76 (d, J=8.4 Hz, 2 H), 7.70 (d, J=8.4 Hz, 2 H), 7.62 (d, J=7.5 Hz, 1 H), 7.55 (dd, J=7.5, 1.8 Hz, 1 H), 6.79 (dd, J=17.4, 10.5 Hz, 1 H), 6.52 (d, J=17.4 Hz, 1 H), 5.91 (d, J=10.5 Hz, 1 H); Mass spectrum: [M+H]+ 247.1.

후처리

  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)

출처 및 근거

ORD 기록
ord-f067bccacd414f35aa5456558863f988
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358263B2

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