Diethyl Ether → 2-Methoxy-2-oxoethyl 2-hydroxy-2-methylbutyrate

HRID 1656716Notes

Reaction equation

[OH:1][C:2]([CH3:11])([CH2:9][CH3:10])[C:3]([O:5][CH2:6][CH2:7]Cl)=[O:4].C(OC)(=O)[CH2:13][OH:14].C(C1C=CC=CC=1)(C)(C)C.C([O:30]CC)C>>[OH:1][C:2]([CH3:11])([CH2:9][CH3:10])[C:3]([O:5][CH2:6][C:7]([O:14][CH3:13])=[O:30])=[O:4]

Participants

Reactant 4

HCID 3283Diethyl Ether

HCID 7366Tert-Butylbenzene

HCID 66774Methyl Glycolate

HCID 189532202-Chloroethyl 2-hydroxy-2-methylbutyrate2×

Product 1

HCID 542931972-Methoxy-2-oxoethyl 2-hydroxy-2-methylbutyrate

Procedure

A 6 mL aliquot of an ethyl ether solution containing 0.25 M 2-chloroethyl 2-hydroxy-2-methylbutyrate, 0.25 M methyl glycolate, and 1.0% tert-butylbenzene was added to 0.4 g Lipase P30. After mixing for 7 d at room temperature, the conversion of 2-chloroethyl 2-hydroxy-2-methylbutyrate to the title compound was estimated (by GC, Method A) to be approximately 10%. The GC peak assigned to the title compound was confirmed by HRMS: calcd for C7H10O5Tms (M--CH3) 247.1001, obsd 247.0998. In identical reactions substituting Lipase MAP10, Lipase G, Lipase AK, or porcine pancreatic lipase for Lipase P30, the relative values for conversions at 7 d (Lipase P30 =100) were 73, 21, 16, and 0, respectively.

Workup

additionwas added to 0.4 g Lipase P30
additionAfter mixing for 7 d at room temperature

Sources & evidence

ORD record: ord-2265363caf6e4315af538900aed40319
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254718

Reaction notes

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