1-Chloro-1-phenylsiletane → HCID 101926025, compound

HRID 257119Notes

Reaction equation

HRID 257119 reaction equation
Cl[Si:2]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[C:6]1([SiH:2]2[CH2:5][CH2:4][CH2:3]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 125979911-Chloro-1-phenylsiletaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 101926025HCID 101926025, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The 1-chloro-1-phenyl-1-silacyclobutane was reacted with lithium aluminum hydride in ethyl ether to obtain 1-phenyl-1-silacyclobutane. The 1-chloro-1-phenyl-1-silacyclobutane (8.4 g, 46 mmole) in 10 ml diethyl ether was added dropwise to 0.87 g 23 mmole of lithium aluminum hydride in 10 ml diethyl ether at ±5° C. The reaction mixture warmed gradually to room temperature. The mixture was stirred over 12 hours. The mixture was hydrolyzed with 3N hydrochloric acid. After separation, the water layer was extracted with 2×20 ml of ethyl ether. The combined organic layer was dried over anhydrous sodium sulfate. Removal of solvent and fractional distillation gave 1-phenyl-1-silacyclobutane. b.p. 70°-72° C./20 mm Hg, 6.3 g, 92% yield was obtained. 1H NMR (δ) 1.39 (m, 4H), 2.31 (m, 2H), 5.25 (m, 1H), 7.46 (m, 3H), 7.70 (m, 2H). 13C NMR (δ) 12.71, 19.67, 127.98, 129.88, 134.35, 135.19, 29Si NMR (δ) -1.80.

Sources & evidence

ORD record
ord-df25879e4b494420a25c14af6c9d5d13
Source dataset
uspto-grants-1993_11
Patent number
US05260377

Reaction notes

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