Isopropyl hydroxyacetate → 2-(1-Methylethoxy)-2-oxoethyl lactate

HRID 1491535Notes

Reaction equation

HRID 1491535 reaction equation
[C:1](OCCCl)(=[O:5])[CH:2]([CH3:4])[OH:3].[C:10]([O:14][CH:15]([CH3:17])[CH3:16])(=[O:13])[CH2:11][OH:12]>C(OCC)C>[C:1]([O:12][CH2:11][C:10]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])(=[O:5])[CH:2]([CH3:4])[OH:3]

Participants

4

Reactant 2

HCID 69338Isopropyl hydroxyacetateHCID 189532282-Chloroethyl 2-hydroxypropanoate2×

Product 1

HCID 541539182-(1-Methylethoxy)-2-oxoethyl lactate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Chloroethyl lactate (1.91 g, 12.5 mmol) and various amounts of isopropyl glycolate (1.48, 2.22 and 2.95 g; 12.5, 18.8 and 25.0 mmol, respectively) in 25 mL of ethyl ether containing 0.125% tert-butylbenzene were added to 1.75 g Lipase P30 powder and the reaction mixtures were agitated on an orbital shaker (175 RPM) at room temperature for 48 hr. After 48 hr, conversion of 2-chloroethyl lactate to the title compound was estimated (by GC, Method A) to be 30, 38 and 44% with 1.0, 1.5 and 2.0 equivalents of isopropyl glycolate, respectively. The GC peak assigned to the title compound was confirmed by HRMS: calcd for C7H10O5Tms (M-CH3) 247.1001, obsd 247.0990. A portion of one of the reactions was partially purified by flash chromatography (ethyl acetate/hexane, 20/80) to give a mixture of 2-chloroethyl lactate and the title compound. The partially purified mixture was separated by flash chromatography (CH2Cl2 /isopropanol, 99/1) to give the title compound: 1H NMR δ1.27 (d, 6H, J=6.3 Hz), δ1.49 (d, 3H, J=7.0 Hz), δ3.28 (d, 1H, J=4.6 Hz), δ4.42 (m, 1H), δ4.60 (d, 1H, J=15.8 Hz),δ4.71 (d, 1H, J=15.8 Hz), δ5.09 (m, 1H, J=6.3 Hz); 13C NMR 20.3, 21.7, 61.5, 66.9, 69.6, 166.8, 174.9.

Workup

  1. customthe reaction mixtures
  2. waitAfter 48 hr

Sources & evidence

ORD record
ord-1a3717a9444d4515b473e77cbf21fbe7
Source dataset
uspto-grants-1994_12
Patent number
US05371001

Reaction notes

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