Triethylamine → 4-Acryloyloxymethyl-2-methoxy-2-phenyl-1,3-dioxolane

HRID 274923Notes

Reaction equation

HRID 274923 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]([O:14][CH3:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4]1.C(N(CC)CC)C.[C:23](Cl)(=[O:26])[CH:24]=[CH2:25]>C(Cl)Cl>[C:23]([O:1][CH2:2][CH:3]1[CH2:7][O:6][C:5]([O:14][CH3:15])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:4]1)(=[O:26])[CH:24]=[CH2:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 214729124-Hydroxymethyl-2-methoxy-2-phenyl-1,3-dioxolane

Product 1

HCID 187799344-Acryloyloxymethyl-2-methoxy-2-phenyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The procedure of Example 1 was repeated, employing 21 grams (100 mmol.) of 4-hydroxymethyl-2-methoxy-2-phenyl-1,3-dioxolane, 25.3 grams (250 mmol.) of triethylamine, 9.5 grams (105 mmol.) of acryloyl chloride and 150 ml. of methylene chloride. The crude product was purified by column chromatography over basic alumina, using 15% (by volume) ethyl acetate in hexane as an eluant, to yield the desired 4-acryloyloxymethyl-2-methoxy-2-phenyl-1,3-dioxolane.

Workup

  1. customThe crude product was purified by column chromatography over basic alumina

Sources & evidence

ORD record
ord-f564e11677bf4cb9913d270d5cfb2a0a
Source dataset
uspto-grants-1995_02
Patent number
US05391616

Reaction notes

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