Triethylamine → Methanesulfonyloxy-acetic acid benzyl ester

HRID 502536Notes

Reaction equation

HRID 502536 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:4])[CH2:2][OH:3].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl>[CH2:6]([O:5][C:1](=[O:4])[CH2:2][O:3][S:21]([CH3:20])(=[O:23])=[O:22])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 561337Benzyl 2-hydroxyacetate

Product 1

HCID 15742138Methanesulfonyloxy-acetic acid benzyl esterYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzyl glycolate (2.0 mL, 14.1 mmol) and triethylamine (2.35 mL, 16.9 mmol) in dichloromethane (30 mL) at 0° C. was added dropwise methanesulfonyl chloride (1.20 mL, 15.1 mL). The reaction was stirred overnight, diluted with dichloromethane, washed with saturated aqueous NH4Cl, and then with saturated NaHCO3, dried with Na2SO4, and concentrated in vacuo to give 2.50 g (73%) of methanesulfonyloxy-acetic acid benzyl ester which was used in the next step without further purification.

Workup

  1. washwashed with saturated aqueous NH4Cl
  2. dry with materialwith saturated NaHCO3, dried with Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9939d3b733c347c388b142a882c23ed1
Source dataset
uspto-grants-2010_08
Patent number
US07776855B2

Reaction notes

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