Triethylamine → 4-(1-Methanesulfonyloxy-2-methyl-butyl)-benzonitrile

HRID 911658Notes

Reaction equation

HRID 911658 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]([C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[CH:8]([CH3:11])[CH2:9][CH3:10].C(N(CC)CC)C>ClCCl.O>[CH3:1][S:2]([O:6][CH:7]([C:12]1[CH:13]=[CH:14][C:15]([C:16]#[N:17])=[CH:18][CH:19]=1)[CH:8]([CH3:11])[CH2:9][CH3:10])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 576562264-(1-Hydroxy-2-methylbutyl)benzonitrile

Product 1

HCID 576560524-(1-Methanesulfonyloxy-2-methyl-butyl)-benzonitrileYield 122%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Add methanesulfonyl chloride (540 mg, 4.72 mmol) to a solution of 4-(1-hydroxy-2-methyl-butyl)-benzonitrile (800 mg, 4.23 mmol) and triethylamine (0.88 mL, 6.35 mmol) in dichloromethane (10 mL) at 0° C. Warm the mixture to room temperature and stir for 1 h. Dilute the mixture with water and dichloromethane. Extract the aqueous layer with dichloromethane. Wash the combined organic extracts with water. Dry the organic solution over Na2SO4, filter and concentrate in vacuo to provide the desired intermediate as a clear oil (1.38 g) that was used without further purification. MS (APCI) m/z: 268 (M+H)+.

Workup

  1. extractionExtract the aqueous layer with dichloromethane
  2. washWash the combined organic extracts with water
  3. dry with materialDry the organic solution over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-a4e6a2badba24dca94d7d1c31981c4be
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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