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

HRID 465631Notes

Reaction equation

HRID 465631 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-7880709dab864c7c9567891b543c49e5
Source dataset
uspto-grants-1992_10
Patent number
US05153290

Reaction notes

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