Glycol monoacetate → Methyl 3-(2-Acetoxyethoxy)-2-hydroxy-3,3-diphenylpropionate

HRID 397329Notes

Reaction equation

HRID 397329 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][CH:8]2[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]([O:23][CH2:24][CH2:25][OH:26])(=[O:22])[CH3:21]>C(OCC)C.B(F)(F)F.CCOCC>[C:20]([O:23][CH2:24][CH2:25][O:26][C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH:8]([OH:13])[C:9]([O:11][CH3:12])=[O:10])(=[O:22])[CH3:21]

Participants

5

Reactant 2

HCID 10960Glycol monoacetateHCID 10587027Methyl 3,3-diphenyloxirane-2-carboxylate

Product 1

HCID 15379666Methyl 3-(2-Acetoxyethoxy)-2-hydroxy-3,3-diphenylpropionate

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

7.95 g (31.3 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate were dissolved in 20 ml of diethyl ether under N2 and cooled to 0° C., and 5.87 ml (31.3 mmol) of 2-hydroxyethyl acetate (50% strength) and 3 drops of BF3.Et2O were added. After removal of the ice bath, the mixture was stirred at RT for 2 h.

Workup

  1. customAfter removal of the ice bath

Sources & evidence

ORD record
ord-85f0a3e4a5b440e2a7a90efbfafe2bdb
Source dataset
uspto-grants-2003_08
Patent number
US06610691B1

Reaction notes

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