Dichloromethane → HCID 11776281, compound

HRID 257434Notes

Reaction equation

HRID 257434 reaction equation
[CH:1]1([O:7][CH2:8][CH2:9][CH2:10][OH:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClCCl.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(N(CC)CC)C>[CH3:15][S:16]([O:11][CH2:10][CH2:9][CH2:8][O:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 100348783-(cyclohexyloxy)propan-1-ol

Product 1

HCID 11776281HCID 11776281, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a solution of 10 parts of 3-(cyclohexyloxy)-1-propanol in 160 parts of dichloromethane there were added 11.2 parts of N,N-diethylethanamine and dropwise 8.14 parts of methanesulfonyl chloride. The whole was stirred for 9 hours at room temperature. The reaction mixture was washed with Na2CO3 (aq.) and water and was then dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 99:1). The eluent of the desired fraction was evaporated and the residue was co-evaporated with methylbenzene. The product was filtered off and dried, yielding 8.6 parts (57.8%) of 3-(cyclohexyloxy)-1-propanol methanesulfonate (ester) (interm. 21).

Workup

  1. washThe reaction mixture was washed with Na2CO3 (aq.) and water
  2. customwas then dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 99:1)
  6. customThe eluent of the desired fraction was evaporated
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-56e0b7c361dd4e79bd420a70a1e7502c
Source dataset
uspto-grants-1993_11
Patent number
US05262418

Reaction notes

Loading…