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

HRID 411887

Reaction equation

HRID 411887 reaction equation
[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]

Participants

5

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 136172,2,4,4-Tetramethyl-1,3-cyclobutanedioneHCID 10942334Sodium Methoxide

Product 1

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

Procedure

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%).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. filtrationThe solid was filtered off with suction
  3. concentrationthe mother liquor was concentrated

Sources & evidence

ORD record
ord-018233e2db2a44b78cd771c96c80a5be
Source dataset
uspto-grants-2003_05
Patent number
US06559343B1

Linked notes

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