Triethylamine → Ethyl 1-{[(methylsulfonyl)oxy]methyl}cyclobutanecarboxylate

HRID 594851Notes

Reaction equation

HRID 594851 reaction equation
[OH:1][CH2:2][C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:19][S:20]([O:1][CH2:2][C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][CH2:4]1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15670506Ethyl 1-(hydroxymethyl)cyclobutane-1-carboxylate

Product 1

HCID 86724246Ethyl 1-{[(methylsulfonyl)oxy]methyl}cyclobutanecarboxylateYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 1-(hydroxymethyl)cyclobutanecarboxylate (1.0 g, 6.3 mmol) and N,N-diethylethanamine (1.5 g, 8.2 mmol) in CH2Cl2 (30 ml) was added methanesulfonyl chloride (869 mg, 7.6 mmol). The mixture was stirred for 6 hours at ambient temperature. After dilution with CHCl3 and H2O, the organic layer was washed with H2O, dried over MgSO4, and concentrated in vacuo to give ethyl 1-{[(methylsulfonyl)oxy]methyl}cyclobutanecarboxylate (1.2 g).

Workup

  1. washAfter dilution with CHCl3 and H2O, the organic layer was washed with H2O
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1c88df22ea84c578606d1a63f83db68
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

Loading…