Triethylamine → 6-Phenylhex-1-yl methylsulfonate

HRID 2209624Notes

Reaction equation

HRID 2209624 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl.CCOCC>[CH3:21][S:22]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5201106-Phenyl-1-hexanol

Product 1

HCID 130797026-Phenylhex-1-yl methylsulfonate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 6-phenyl-1-hexanol (3.2g; 18 mmol) dissolved in CH2Cl2 (60 ml) is added Et3N (3.7 ml) and the solution is cooled to 0° C. Methanesulfonyl chloride (1.5 ml; 20 mmol) is added dropwise and then the reaction mixture is allowed to stir for 30 minutes at 0° C. This is then diluted with Et2O and washed with 2N HCl, NaHCO3 solution 2× and brine, dried (MgSO4) and concentrated to dryness to obtain 6-phenylhex-1-yl methylsulfonate as an oil which is used directly in Step E.

Workup

  1. washwashed with 2N HCl, NaHCO3 solution 2× and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e47c30cb286c40dda34008f4ca07f434
Source dataset
uspto-grants-1995_10
Patent number
US05455260

Reaction notes

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