Triethylamine → 2-(Prop-2-ynyloxy)ethyl methanesulfonate

HRID 1971688Notes

Reaction equation

HRID 1971688 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][OH:7])[C:2]#[CH:3].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(OCC)C.O>[CH3:15][S:16]([O:7][CH2:6][CH2:5][O:4][CH2:1][C:2]#[CH:3])(=[O:18])=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 775962-Propynoxyethanol

Product 1

HCID 866505712-(Prop-2-ynyloxy)ethyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.7 g of 11b and 3 ml of triethyl amine in 20 ml of diethyl ether was treated at 0° C. with 1.5 ml of methanesulfonyl chloride. The mixture was stirred for an additional 30 min and then diluted with 35 ml of water and extracted with ethyl acetate. The combined organic layers were washed with 1M aq. K2CO3 solution and water, dried and concentrated, to provide 2.45 of 11c as a colorless oil; Rf 0.45 (heptane/ethyl acetate 1/1).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with 1M aq. K2CO3 solution and water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1f68b330314f45c9b6cecca358262577
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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