Triethylamine → 2-[(Methylsulfonyl)oxy]-5-hexynenitrile

HRID 615549Notes

Reaction equation

HRID 615549 reaction equation
[OH:1][CH:2]([CH2:5][CH2:6][C:7]#[CH:8])[C:3]#[N:4].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([O:1][CH:2]([CH2:5][CH2:6][C:7]#[CH:8])[C:3]#[N:4])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 130449482-Hydroxy-5-hexynenitrile

Product 1

HCID 130449492-[(Methylsulfonyl)oxy]-5-hexynenitrileYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 2-hydroxy-5-hexynenitrile (8.0 g, 73.3 mmol) and dry triethylamine (10.1 g, 0.1 mol) in 50 ml of dry CH2Cl2 was treated with a solution of methanesulfonyl chloride (10.3 g, 90 mmol) in 50 ml of CH2Cl2, at 0° C. for 11/2 h. The reaction mixture was diluted with CH2Cl2, washed twice with cold 1.0N H2SO4, twice with water, and dried over MgSO4. The filtered CH2Cl2 solution was concentrated at 40° C./30 mm to give 12 g of pale yellow liquid. Purification of this material on 220 g of silica gel and eluted with ether-petroleum ether (1:1 parts by volume) gave 8.7 g (56% by weight yield from pentynal) of 2-[(methylsulfonyl)]-5-hexynenitrile as a colorless liquid.

Workup

  1. washwashed twice with cold 1.0N H2SO4, twice with water
  2. dry with materialdried over MgSO4
  3. concentrationThe filtered CH2Cl2 solution was concentrated at 40° C./30 mm

Sources & evidence

ORD record
ord-bc5064ebef77485db2f8886dbf5b8c68
Source dataset
uspto-grants-1985_02
Patent number
US04500462

Reaction notes

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