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

HRID 265809

Reaction equation

[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]

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-03a3bb5d7b4f4ec0af10439e9aa05936
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05648514

Linked notes

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