Diethyl Ether → HCID 53961620, compound

HRID 1656712Notes

Reaction equation

HRID 1656712 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 0.25 M 2-chloroethyl 2-hydroxy-2-methylpropionate, 0.25 M 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-e3c258e9b3714d84a36fbf454d87c97d
Source dataset
uspto-grants-1993_10
Patent number
US05254718

Reaction notes

Loading…