Trimethylsilyl cyanide → 4-[(5-Cyano-7,8-dihydro-8,8-dimethylnaphth-3-yl)ethynyl]benzoic acid

HRID 265809

반응식

HRID 265809 반응식
[CH3:1][C:2]1([CH3:24])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5](=O)[CH2:4][CH2:3]1.[C:25]([Si](C)(C)C)#[N:26]>B(F)(F)F.CCOCC>[C:25]([C:5]1[C:6]2[CH:7]=[C:8]([C:12]#[C:13][C:14]3[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:21][CH:22]=3)[CH:9]=[CH:10][C:11]=2[C:2]([CH3:24])([CH3:1])[CH2:3][CH:4]=1)#[N:26]

참가 물질

4

반응물 2

HCID 82115Trimethylsilyl cyanideHCID 183145934-[(5,6,7,8-Tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoic acid2회

생성물 1

HCID 230017714-[(5-Cyano-7,8-dihydro-8,8-dimethylnaphth-3-yl)ethynyl]benzoic acid

시약·촉매·용매 1

HCID 8000Boron trifluoride etherate촉매

반응 조건

온도
80 °C

실험 절차

To 76 mg (0.24 mmol) of 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoic acid (Compound 8) was added 0.06 ml (0.48 mmol) of cyanotrimethylsilane and 6 drops of boron trifluoride etherate. The resulting dark mixture was heated at 80° C for 45 minutes, cooled to room temperature and purified by flash chromatography (silica, 50% EtOAc-hexane) to yield the title compound as a yellow solid.

후처리

  1. temperaturecooled to room temperature
  2. custompurified by flash chromatography (silica, 50% EtOAc-hexane)

출처 및 근거

ORD 기록
ord-03a3bb5d7b4f4ec0af10439e9aa05936
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648514

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