Methyl Glycolate → HCID 53694930, compound

HRID 326783Notes

Reaction equation

HRID 326783 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][OH:3].C(N(CC)C(C)C)(C)C.Cl[C:17]([O:19][CH:20]([Cl:22])[CH3:21])=[O:18]>O1CCCC1>[Cl:22][CH:20]([O:19][C:17]([O:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])=[O:18])[CH3:21]

Participants

5

Reactant 3

HCID 66774Methyl GlycolateHCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 53694930HCID 53694930, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-water bath cooled solution of methyl glycolate (13.5 mL) and N,N-diisopropylethylamine (30.46 mL) in tetrahydrofuran (180 mL) was added dropwise with stirring 25.0 g of 1-chloroethyl chloroformate. The 0° C. bath was removed, and the mixture stirred for an additional 3 hr. After filtration to remove insoluble amine hydrochloride, the THF solution was evaporated under reduced pressure. The residue was dissolved in a mixture of ethyl acetate and water. The ethyl acetate layer was separated, dried over anh. sodium sulfate, and evaporated under reduced pressure to give 31.1 g of reddish oil. NMR.

Workup

  1. additionwas added dropwise
  2. customThe 0° C. bath was removed
  3. filtrationAfter filtration
  4. customto remove insoluble amine hydrochloride
  5. customthe THF solution was evaporated under reduced pressure
  6. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  7. customThe ethyl acetate layer was separated
  8. dry with materialdried over anh. sodium sulfate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a934749561154fefbb4eabbe841976f1
Source dataset
uspto-grants-1993_12
Patent number
US05270331

Reaction notes

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