Diethyl Ether → 2-Methoxy-2-oxoethyl lactate

HRID 1491533Notes

Reaction equation

HRID 1491533 reaction equation
[C:1]([O:6][CH2:7][CH2:8]Cl)(=[O:5])[CH:2]([CH3:4])[OH:3].C(OC)(=O)[CH2:11][OH:12].C([O:18]CC)C>>[C:1]([O:6][CH2:7][C:8]([O:12][CH3:11])=[O:18])(=[O:5])[CH:2]([CH3:4])[OH:3]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 66774Methyl Glycolate2×HCID 189532282-Chloroethyl 2-hydroxypropanoate

Product 1

HCID 197888162-Methoxy-2-oxoethyl lactate

Procedure

2-Chloroethyl lactate (19.10 g, 0.125 mol) and methyl glycolate (11.26 g, 0.125 mol) in 250 mL of ethyl ether containing 0.125% tert-butylbenzene was added to 17.5 g Lipase P30 powder in duplicate reactions. The reaction mixtures were agitated on an orbital shaker (175 RPM) at room temperature for 8 hr and an additional equivalent of methyl glycolate was added. After agitation for a further 40 hr, the enzyme powders were removed by filtration and the filtrates were combined and evaporated. The resulting residue was chromatographed by flash chromatography (ethyl acetate/hexane, 22.5/77.5) to give the title compound as an oil (6.00 g, 15%- an approximately equal amount of product was recovered in fractions which also contained methyl glycolate): 1H NMR δ1.49 (d, 3H, J=7.0 Hz), δ3.55 (bs, 1H), δ3.78 (s, 3H), δ4.43 (q, 1H, J=6.9 Hz), δ4.67 (d, 1H, J=15.9 Hz), δ4.76 (d, 1H, J=15.9 Hz); 13C NMR 20.04, 52.09, 60.87, 66.67, 167.63, 174.62; HRMS calcd for C5H6O5Tms (M-CH3) 219.0688, obsd 219.0641.

Workup

  1. customThe reaction mixtures
  2. waitAfter agitation for a further 40 hr
  3. customthe enzyme powders were removed by filtration
  4. customevaporated
  5. customThe resulting residue was chromatographed by flash chromatography (ethyl acetate/hexane, 22.5/77.5)

Sources & evidence

ORD record
ord-5529a090bf304633bffea8f9b491b81b
Source dataset
uspto-grants-1994_12
Patent number
US05371001

Reaction notes

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