Pyridine → HCID 86649327, compound

HRID 1797838Notes

Reaction equation

HRID 1797838 reaction equation
[OH:1][CH:2]([CH2:10][CH3:11])[C:3]#[C:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].N1C=CC=CC=1.[C:18](Cl)(=[O:20])[CH3:19]>ClCCl>[C:18]([O:1][CH:2]([CH2:10][CH3:11])[C:3]#[C:4][CH2:5][C:6]([O:8][CH3:9])=[O:7])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 86649328HCID 86649328, compound

Product 1

HCID 86649327HCID 86649327, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 355 mg (2.5 mmol) of methyl 4-hydroxyhex-2-ynecarboxylate (cf. J. Kunes et al., Coll. Czech. Chem. Comm. 66, 1809-1830, 2001) and 243 μl (3 mmol) of pyridine in 25 ml of dichloromethane is slowly admixed at 0° C. with 196 μl (3 mmol) of acetyl chloride. After 16 h at room temperature, the mixture is washed successively with dilute aqueous sulphuric acid and sodium hydrogencarbonate solution. Drying over magnesium sulphate and concentrating the organic phase affords 410 mg (89% of theory) of methyl 4-acetoxyhex-2-ynecarboxylate.

Workup

  1. washthe mixture is washed successively with dilute aqueous sulphuric acid and sodium hydrogencarbonate solution
  2. dry with materialDrying over magnesium sulphate
  3. concentrationconcentrating the organic phase

Sources & evidence

ORD record
ord-7f73e9ab622e4202b27fd77cb76bd400
Source dataset
uspto-grants-2013_01
Patent number
US08343893B2

Reaction notes

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