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

HRID 6191Notes

Reaction equation

HRID 6191 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 A 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-0ab8bbc1253f48d2a40e581350c80b04
Source dataset
uspto-grants-1993_09
Patent number
US05247006

Reaction notes

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