Triethylamine → 6-Methylsulfonyloxy-5-(2-propenyl)-hexanenitrile

HRID 1494144Notes

Reaction equation

HRID 1494144 reaction equation
[OH:1][CH2:2][CH:3]([CH2:9][CH:10]=[CH2:11])[CH2:4][CH2:5][CH2:6][C:7]#[N:8].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:19][S:20]([O:1][CH2:2][CH:3]([CH2:9][CH:10]=[CH2:11])[CH2:4][CH2:5][CH2:6][C:7]#[N:8])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14986704HCID 14986704, compound

Product 1

HCID 149867056-Methylsulfonyloxy-5-(2-propenyl)-hexanenitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2679 g of 6-hydroxy-5-(2-propenyl)-hexanenitrile in 25 L of methylene chloride is added 2681 mL of triethylamine. The mixture is cooled to -10° in an ice salt bath and a solution of 2103 g of methanesulfonyl chloride in 2 L of methylene chloride is added dropwise over 3 hours keeping the temperature at -5°. After addition is complete, the mixture is stirred for 3 hours in an ice salt bath and then overnight at 10°. The mixture is washed with water, saturated sodium bicarbonate solution, water and then brine, dried over sodium sulfate, evaporated to dryness, and dried at 45°/3 mm Hg to yield 6-methanesulfonyloxy-5-(2-propenyl)-hexanenitrile.

Workup

  1. temperatureThe mixture is cooled to -10° in an ice salt bath
  2. customat -5°
  3. additionAfter addition
  4. customovernight
  5. customat 10°
  6. washThe mixture is washed with water, saturated sodium bicarbonate solution, water
  7. dry with materialbrine, dried over sodium sulfate
  8. customevaporated to dryness
  9. customdried at 45°/3 mm Hg

Sources & evidence

ORD record
ord-57a30508f1694a53a2db3452b7fbd8f4
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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