2-Methoxyethanol → tert-Butyl 2-(2-methoxyethoxymethyl)acrylate

HRID 374344Notes

Reaction equation

Br[CH2:2][C:3](=[CH2:11])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][CH2:20][CH2:21][OH:22]>O>[CH3:18][O:19][CH2:20][CH2:21][O:22][CH2:2][C:3](=[CH2:11])[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 2-(bromomethyl)acrylate (2.0 g, 9.0 mmol) in 2-methoxyethanol (30 ml) at 0° C. was added, in one portion, potassium carbonate (2.5 g, 18 mmol) and the mixture stirred at 0° C. for 1 hour. The reaction was diluted with distilled water (100 ml) and extracted with dichloromethane (100 ml). The layers were separated and the aqueous layer further extracted with dichloromethane (2×50 ml). The combined organic extracts were dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica by eluting with hexane/ethyl acetate (2:1) to give, after combination and evaporation of appropriate fractions, the title compound as a yellow oil, (1.6 g, 82%). Rf. 0.32 (silica, hexane/ethyl acetate, 2:1). 1H-NMR (300 MHz, CDCl3) 1.50 (s, 9H), 3.42 (s, 3H) , 3.56-3.63 (m, 2H), 3.65-3.74 (m, 2H), 4.25 (s, 2H), 5.84 (s, 1 H), 6.25 (s, 1H) ppm.

Workup

extractionextracted with dichloromethane (100 ml)
customThe layers were separated
extractionthe aqueous layer further extracted with dichloromethane (2×50 ml)
dry with materialThe combined organic extracts were dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on silica
washby eluting with hexane/ethyl acetate (2:1)
customto give
customafter combination and evaporation of appropriate fractions

Sources & evidence

ORD record: ord-06bbc94676984a0b90ae259620110917
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166406

Reaction notes

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