Acetic Acid → AG-G-75877

HRID 851361Notes

Reaction equation

HRID 851361 reaction equation
[CH3:1][Si:2]([CH2:5][C:6](=[CH2:11])[CH2:7][C:8]([OH:10])=[O:9])([CH3:4])[CH3:3].[N+](=[CH2:14])=[N-].C(O)(=O)C>C(OCC)C>[CH3:1][Si:2]([CH2:5][C:6](=[CH2:11])[CH2:7][C:8]([O:10][CH3:14])=[O:9])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550Diazomethane2×HCID 111165293-Butenoic acid, 3-[(trimethylsilyl)methyl]-

Product 1

HCID 11769254AG-G-75877

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 3-(trimethylsilylmethyl)but-3-enoic acid (36.5 g) in diethyl ether (200 ml) at 10°-15° C. was added a solution of diazomethane in diethyl ether (ca 0.6 M solution, 400 ml). The excess of diazomethane was decomposed by addition of acetic acid. The resultant solution was concentrated in vacuo to 200 ml and the concentrate was washed with an aqueous sodium bicarbonate and brine. Drying over magnesium sulfate and evaporation of the solvent left a yellow oil, which was distilled in vacuo to give methyl 3-(trimethylsilylmethyl)but-3-enoate (34.74 g) as a colorless oil, bp 74°-75° C. (10 Torr).

Workup

  1. concentrationThe resultant solution was concentrated in vacuo to 200 ml
  2. washthe concentrate was washed with an aqueous sodium bicarbonate and brine
  3. dry with materialDrying over magnesium sulfate and evaporation of the solvent
  4. waitleft a yellow oil, which
  5. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-258b9423f7ee4c4097dd9bb67fd7f7f5
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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