Trimethylsilyl cyanide → 4-[(7,8-Dihydro-8,8-dimethyl-5-trimethylsiloxynaphth-3-yl)ethynyl]benzoic acid

HRID 53391

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:23])[CH2:4][CH2:3]1.[C:25]([Si:27](C)([CH3:29])[CH3:28])#N>C1COCC1.[I-].[Zn+2].[I-]>[CH3:1][C:2]1([CH3:24])[C:11]2[CH:10]=[CH:9][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:7][C:6]=2[C:5]([O:23][Si:27]([CH3:29])([CH3:28])[CH3:25])=[CH:4][CH2:3]1

Participants

Conditions

Temperature: 25 °C

Procedure

To a cold solution (0° C.) of 50 mg (0.07 mmol) of zinc iodide (dried in vacuo over P2O5 for several hours) in 2 ml of dry THF (flushed with argon) was added a solution of 0.110 g (0.34 mmol) of 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoic acid (Compound 8) in 2 ml of THF followed by 0.14 ml (1.03 mmol) of cyanotrimethylsilane. The resulting mixture was stirred at 25° C. for 12 hours and purified by flash chromatography (silica, 50% EtOAc-hexane) to yield the title compound as a white solid.

Workup

custompurified by flash chromatography (silica, 50% EtOAc-hexane)

Sources & evidence

ORD record: ord-35939b1acb954bdebea6354ff1e69bdf
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618931

Linked notes

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