Diethyl Ether → HCID 53961620, compound

HRID 1491538Notes

Reaction equation

HRID 1491538 reaction equation
[OH:1][C:2]([CH3:10])([CH3:9])[C:3]([O:5][CH2:6][CH2:7]Cl)=[O:4].C(OC)(=O)[CH2:12][OH:13].C(C1C=CC=CC=1)(C)(C)C.C([O:29]CC)C>>[OH:1][C:2]([CH3:10])([CH3:9])[C:3]([O:5][CH2:6][C:7]([O:13][CH3:12])=[O:29])=[O:4]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 7366Tert-ButylbenzeneHCID 66774Methyl GlycolateHCID 18953229HCID 18953229, compound2×

Product 1

HCID 53961620HCID 53961620, compound

Procedure

A 6 mL aliquot of an ethyl ether solution containing 0.25M 2-chloroethyl 2-hydroxy-2-methylpropionate, 0.25M methyl glycolate, and 0.125% tert-butylbenzene was added to 0.5 g Lipase P30. After mixing for 48 hr at room temperature, the conversion of 2-chloroethyl 2-hydroxy-2-methylpropionate to the title compound was estimated (by GC, Method A) to be 47%. The GC peak assigned to the title compound was confirmed by HRMS: calcd for C6H10O5Tms (M-CH3) 233.0845, obsd 233.0870. In identical reactions substituting Lipase AK, Lipase MAP10, Lipase G, Lipase AP12, Protease M, or porcine pancreatic lipase for Lipase P30, the relative values for conversions at 48 hr (Lipase P30=100) were 33, 32, 16, 14, 13 and 2, respectively.

Workup

  1. additionwas added to 0.5 g Lipase P30
  2. additionAfter mixing for 48 hr at room temperature

Sources & evidence

ORD record
ord-9e6927fca3014734b1ba2ec5b90ee9e9
Source dataset
uspto-grants-1994_12
Patent number
US05371001

Reaction notes

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