Water → 4-(4-Cyanophenyl)butyl methanesulfonate

HRID 500473Notes

Reaction equation

HRID 500473 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1.C(N(CC)CC)C.O>ClCCl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 185403804-(4-Hydroxybutyl)benzonitrile

Product 1

HCID 185404244-(4-Cyanophenyl)butyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (2.32 mL, 30 in mmol) was added to a cooled (0° C.), stirred solution of 4-(4-hydroxybutyl)benzonitrile (from step (ii) above, 5.2 g, 29.7 mmol) and triethylamine (4.35 mL) in dichloromethane (50 mL). The resulting, mixture was stirred for 4 h before water (150 mL) was added, and the organic layer separated, dried and concentrated to give the sub-title compound. This product was used directly in the next step without further purification.

Workup

  1. additionwas added
  2. customthe organic layer separated
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-73951895fb8043c9807dfd3d8a437746
Source dataset
uspto-grants-2010_08
Patent number
US07772229B2

Reaction notes

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