Triethylamine → HCID 22381912, compound

HRID 1032903Notes

Reaction equation

HRID 1032903 reaction equation
[CH:1]1([CH2:5][OH:6])[CH2:4][CH2:3][CH2:2]1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].C(N(CC)CC)C>CCOCC>[CH3:7][S:8]([O:6][CH2:5][CH:1]1[CH2:4][CH2:3][CH2:2]1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 78130Cyclobutylcarbinol

Product 1

HCID 22381912HCID 22381912, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cyclobutanemethanol (24.9 g; 0.287 mol) and methanesulfonyl chloride (35.3 g; 0.302 mol) in dry ether (250 ml) was cooled to -20° C. under dry nitrogen. Triethylamine (44 ml; 0.32 mol) was added dropwise over 15 min with external cooling so that the reaction temperature remained below -5° C. The reaction mixture was allowed to warm to room temperature over 1 h and then filtered. The remaining solid was washed with ether. The ether solutions were combined and the ether evaporated, to afford crude cyclobutylmethyl methanesulfonate (48.75 g) as a pale yellow liquid, which was used in the next step without further purification. NMR - d(CDCl3 ; 60 MHz) 1.6-2.9 (7H, m), 3.0 (3H, s) and 4.1 (2H, d, J=7 Hz).

Workup

  1. temperaturewith external cooling so that the reaction temperature
  2. customremained below -5° C
  3. filtrationfiltered
  4. washThe remaining solid was washed with ether
  5. customthe ether evaporated

Sources & evidence

ORD record
ord-78572052a87842bdaea973ef1123dcfb
Source dataset
uspto-grants-1994_05
Patent number
US05308830

Reaction notes

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