Chlorotrimethylsilane → Methyl 2,2,4-Trimethyl-3-silyloxypent-3-enecarboxylate

반응식

[CH3:1][C:2]1([CH3:10])[C:5](=O)[C:4]([CH3:8])([CH3:7])[C:3]1=[O:9].[CH3:11][O-:12].[Na+].C[Si:15](Cl)(C)C.[O:19]1[CH2:23]CCC1>>[CH3:10][C:2]([CH3:1])([C:3]([O:9][SiH3:15])=[C:4]([CH3:7])[CH3:8])[CH2:5][C:11]([O:19][CH3:23])=[O:12]

참가 물질

반응물 4

HCID 6397Chlorotrimethylsilane

HCID 8028Tetrahydrofuran

HCID 136172,2,4,4-Tetramethyl-1,3-cyclobutanedione

HCID 10942334Sodium Methoxide

생성물 1

HCID 123759875Methyl 2,2,4-Trimethyl-3-silyloxypent-3-enecarboxylate

실험 절차

84 g (0.6 mol) of 2,2,4,4-tetramethylcyclobutane-1,3-dione and 32.4 g (0.6 mol) of sodium methylate were mixed together in 320 ml of tetrahydrofuran. 65.1 g (0.6 mol) of trimethylsilyl chloride were added dropwise and the mixture was stirred. The reaction mixture was then concentrated and the residue was taken up with diethyl ether. The solid was filtered off with suction and the mother liquor was concentrated. Yield: 135 g (89%).