Acetic Anhydride → Ethyl 3-ethoxy-2-(methanesulfonyl)prop-2-enoate

HRID 1297695Notes

Reaction equation

HRID 1297695 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7])[CH3:2].[CH:11](OCC)(OCC)[O:12][CH2:13][CH3:14].C(OC(=O)C)(=O)C>>[CH2:1]([O:3][C:4](=[O:10])[C:5]([S:6]([CH3:9])(=[O:8])=[O:7])=[CH:11][O:12][CH2:13][CH3:14])[CH3:2]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 78201Ethyl methanesulfonylacetate

Product 1

HCID 71353473Ethyl 3-ethoxy-2-(methanesulfonyl)prop-2-enoate

Conditions

Temperature
135 °C

Procedure

A mixture of methanesulfonyl-acetic acid ethyl ester (example 61b) (90 g, 0.547 mol), triethyl orthoformate (242.9 g, 0.641 mol), and acetic anhydride (227 mL) was heated at 130-140° C. for three hours. After cooling the reaction to room temperature, solvent was removed under reduced pressure to give 3-ethoxy-2-methanesulfonyl-acrylic acid ethyl ester (purity 50%). The crude compound was used in the following reaction without further purification. LC-MS m/e 223 (MH+).

Workup

  1. temperatureAfter cooling
  2. customthe reaction to room temperature
  3. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-72ab3f79ef514a6992d1ebec49bdff3f
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

Loading…