Methyl Acrylate → Methyl-2-methoxy-4-[(trimethylsilyl)oxy]cyclohex-3-ene-1-carboxylate

HRID 712047

Reaction equation

HRID 712047 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[CH3:7][O:8][CH:9]=[CH:10][C:11]([O:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH2:12]>C1(C)C=CC=CC=1>[CH3:6][O:5][C:1]([CH:2]1[CH2:3][CH2:12][C:11]([O:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]1[O:8][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 1010511-Methoxy-3-trimethylsilyloxy-1,3-butadiene

Product 1

HCID 15496370Methyl-2-methoxy-4-[(trimethylsilyl)oxy]cyclohex-3-ene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl acrylate (5.23 mL, 58.0 mmol) and 1-methoxy-3-(trimethylsiloxy)-1,3-butadiene (from Aldrich, 10.0 g, 58.0 mmol) in toluene (100 mL) was heated at 80° C. for 2 d. The reaction solution was concentrated and purified on silica gel column to give the desired product as a mixture of trans- and cis-isomers (8.3 g, 55%). 1H NMR (500 MHz, CDCl3) δ 5.16 (1H, m), 4.97 (1H, m), 4.22 (1H, m), 4.08 (1H, m), 3.68 (3H, s), 3.67 (3H, s), 3.32 (3H, s), 3.24 (3H, s), 2.59 (1H, m), 2.51 (1H, m), 1.80-2.14 (8H, m), 0.18 (18H, s) ppm.

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified on silica gel column

Sources & evidence

ORD record
ord-0b335b29582d49b5abad380ade4b8dff
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Linked notes

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