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

HRID 1171841Notes

Reaction equation

HRID 1171841 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].BrCC1(CC(OC)=O)CC1>ClCCl.O>[CH3:18][S:19]([O:1][CH2:2][C:3]1([CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH2:5][CH2:4]1)(=[O:21])=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 16115999Methyl 1-(bromomethyl)cyclopropaneacetateHCID 29941748(1-Hydroxymethylcyclopropyl)acetic acid methyl ester2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

8.45 g of crude methyl 2-[1-(hydroxymethyl)cyclopropyl]acetate (compound 14a) was dissolved in 85 ml dry dichloromethane. The pale yellow solution was cooled to 0° C. Then, 7.71 g triethylamine was added and 8.05 g methanesulfonyl chloride was added dropwise over 8 minutes. The yellow suspension was stirred at 0° C. TLC showed that after 10 minutes the reaction was completed. To the reaction mixture, 35 ml water and 20 ml dichloromethane were added. The water layer was washed with 20 ml dichloromethane. The combined organic layers were washed with 30 ml water, dried (Na2SO4) and evaporated to dryness, resulting in a yellow oil. The product was immediately used in the next step (synthesis of methyl 1-(bromomethyl)-cyclopropaneacetate).

Workup

  1. customafter 10 minutes
  2. washThe water layer was washed with 20 ml dichloromethane
  3. washThe combined organic layers were washed with 30 ml water
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customresulting in a yellow oil

Sources & evidence

ORD record
ord-8345a0a4e34e4e568e9101147db97ce2
Source dataset
uspto-grants-2010_11
Patent number
US07829716B2

Reaction notes

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