Methyl but-2-ynoate → Methyl 2-methyl-4-trimethylsilyloxybenzoate

HRID 1739770Notes

Reaction equation

HRID 1739770 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[O:3][C:4]1[CH:9]=CC[CH2:6][CH:5]=1.[C:12]([O:17][CH3:18])(=[O:16])[C:13]#[C:14][CH3:15]>C1(C)C=CC=CC=1>[CH3:15][C:14]1[CH:9]=[C:4]([O:3][Si:2]([CH3:11])([CH3:10])[CH3:1])[CH:5]=[CH:6][C:13]=1[C:12]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 141019Methyl but-2-ynoateHCID 40956562-(Trimethylsiloxy)-1,3-cyclohexadiene

Product 1

HCID 21879730Methyl 2-methyl-4-trimethylsilyloxybenzoateYield 67.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

A 50 mL round bottom flask equipped with magnetic stir bar and condenser was charged with 6.0 g of 2-trimethylsilyloxy-1,3-cyclohexadiene, 3.5 g methyl tetrolate in 3 mL dry toluene. The reaction was heated to 150° C. for 50 hours at which point 1H-NMR indicated no starting diene. The raction was concentrated in vacuo to provide 5.7 g (67%) methyl 2-methyl-4-trimethylsilyloxybenzoate.

Workup

  1. customA 50 mL round bottom flask equipped with magnetic stir bar and condenser
  2. concentrationThe raction was concentrated in vacuo

Sources & evidence

ORD record
ord-6aa9e3c997d249a79f568666bd8ae218
Source dataset
uspto-grants-1999_10
Patent number
US05968942

Reaction notes

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