Triethylamine → Methyl 2-(1-[(methanesulfonyloxy)-methyl]cyclopropyl)acetate

HRID 1798457Notes

Reaction equation

HRID 1798457 reaction equation
[OH:1][CH2:2][C:3]1([CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:10][O:9][C:7](=[O:8])[CH2:6][C:3]1([CH2:2][O:1][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 29941748(1-Hydroxymethylcyclopropyl)acetic acid methyl ester

Product 1

HCID 58203553Methyl 2-(1-[(methanesulfonyloxy)-methyl]cyclopropyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl [1-(hydroxymethyl)cyclopropyl]acetate (1 eq.) from the previous step in DCM (0.1 M) at −40° C. was added triethylamine (3 eq.) and then methanesulfonyl chloride (1.5 eq.). The reaction was warmed to 0° C. over 1 h, and it was diluted with DCM and quenched with saturated aqueous NaHCO3. The aqueous phase was extracted with DCM. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 0%→50% EtOAc in Hex) to afford the title compound appendage 3 as an oil.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionThe aqueous phase was extracted with DCM
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography (SiO2, 0%→50% EtOAc in Hex)

Sources & evidence

ORD record
ord-464bb27b60e64b42882fa7377fbbe647
Source dataset
uspto-grants-2013_01
Patent number
US08343968B2

Reaction notes

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