Diethyl Ether → HCID 53961620, compound

HRID 1656713Notes

Reaction equation

HRID 1656713 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([O:19]CC)C>>[OH:1][C:2]([CH3:10])([CH3:9])[C:3]([O:5][CH2:6][C:7]([O:13][CH3:12])=[O:19])=[O:4]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 66774Methyl GlycolateHCID 18953229HCID 18953229, compound

Product 1

HCID 53961620HCID 53961620, compound

Procedure

2-Chloroethyl 2-hydroxy-2-methylpropionate, prepared as described in Step 1 of Example 3a, (5.22 g, 31.3 mmol) and methyl glycolate (2.83 g, 31.4 mmol) in 125 mL of ethyl ether containing 0.125% tert-butylbenzene was added to 9.0 g Lipase P30 and the reaction mixture was agitated on an orbital shaker for 4d. The enzyme powder was removed by filtration, the solvent was removed, and a portion of the resulting residue was purified by flash chromatography (ethyl acetate:hexane, 20/80) to give the title compound as an oil: 1H NMR δ 1.51 (s, 6H), δ 3.14 (s, 1H), δ 3.78 (s, 3 H), δ 4.71 (s, 2H); 13C NMR 27.0, 52.1, 61.1, 72.1, 167.6, 176.4 ppm.

Workup

  1. additionwas added to 9.0 g Lipase P30
  2. customThe enzyme powder was removed by filtration
  3. customthe solvent was removed
  4. customa portion of the resulting residue was purified by flash chromatography (ethyl acetate:hexane, 20/80)

Sources & evidence

ORD record
ord-70017d761f2b44e7b90051cc60278c3f
Source dataset
uspto-grants-1993_10
Patent number
US05254718

Reaction notes

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