Chlorotrimethylsilane → HCID 16731313, compound

HRID 1107726Notes

Reaction equation

C([Li])CCC.C(NC(C)C)(C)C.[C:13]([C:15]1[S:16][CH:17]=[CH:18][C:19]=1[CH3:20])#[N:14].[CH3:21][Si:22](Cl)([CH3:24])[CH3:23]>C1COCC1.CN1CCCN(C)C1=O>[C:13]([C:15]1[S:16][C:17]([Si:22]([CH3:24])([CH3:23])[CH3:21])=[CH:18][C:19]=1[CH3:20])#[N:14]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (1.45M in hexanes, 51.9 ml) was added dropwise to a stirred solution of diisopropylamine (11.7ml, 83.0 mmol) in dry THF (150 ml) at -5-0° C. and the solution stirred for 30 min. 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) (13.6 ml, 0.11 mmol) was added, the mixture was cooled to -78° C. and a solution of 2-cyano-3-methylthiophene (9.27 g, 75.4 mmol) in THF (20 ml) added dropwise, followed by trimethylsilylchloride (19.1 ml) after 30 sec. The mixture was warmed to room temperature over 30 min., evaporated, taken up in diethyl ether, the solids filtered off and the filtrate evaporated to afford a yellow oil. This was purified by flash chromatography on untreated neutral alumina, eluting with 1% diethyl ether in hexane, to give 2-cyano-3-methyl-5-trimethylsilylthiophene as a clear oil (6.52 g). M+ 195; 360 MHz 1H n.m.r. (CDCl3) 7.02 (1H, s), 2.43 (3H, s), 0.33 (9H, s).

Workup

temperatureThe mixture was warmed to room temperature over 30 min.
customevaporated
filtrationthe solids filtered off
customthe filtrate evaporated
customto afford a yellow oil
customThis was purified by flash chromatography on untreated neutral alumina
washeluting with 1% diethyl ether in hexane

Sources & evidence

ORD record: ord-3c250953b65040188431ab3be0ae8da1
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06063789

Reaction notes

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