Triethylamine → 6-Phenylhex-1-yl methylsulfonate

HRID 1734675Notes

Reaction equation

HRID 1734675 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 (3.2 g; 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 2x and brine, dried (MgSO4) and concentrated to dryness to obtain 6-phenylhex-1-yl methylsuifonate as an oil which is used directly in Step E.

Workup

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

Sources & evidence

ORD record
ord-1dd5719fcd6f4c778d409b04e02e6df9
Source dataset
uspto-grants-1996_07
Patent number
US05534532

Reaction notes

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