3-Butyn-1-OL → HCID 131716816, compound

HRID 1084332Notes

Reaction equation

HRID 1084332 reaction equation
Br[C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[OH:16][CH2:17][CH2:18][C:19]#[CH:20]>C(Cl)Cl>[OH:16][CH2:17][CH2:18][C:19]#[C:20][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 135663-Butyn-1-OLHCID 14256374HCID 14256374, compound

Product 1

HCID 131716816HCID 131716816, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

461 mg of dimethyl 5-bromopyridine-2,4-dicarboxylate (from Example 3) and 142 mg of 4-hydroxy-1-butyne are dissolved in methylene chloride in a flask flushed with argon, and 680 μl of triethylamine are added dropwise. The mixture is stirred at room temperature for 15 minutes, 13 mg of ((C6H5)3P)2PdCl2 and 2 mg of CuI are added and the mixture is boiled under reflux for 2 hours. After cooling, the mixture is diluted with methylene chloride and washed with water and sodium chloride solution and the combined organic phases are dried over potassium carbonate. After the solvent has been evaporated off, 347 mg of a white solid remain.

Workup

  1. customflushed with argon, and 680 μl of triethylamine
  2. additionare added dropwise
  3. addition13 mg of ((C6H5)3P)2PdCl2 and 2 mg of CuI are added
  4. temperatureunder reflux for 2 hours
  5. temperatureAfter cooling
  6. additionthe mixture is diluted with methylene chloride
  7. washwashed with water and sodium chloride solution
  8. dry with materialthe combined organic phases are dried over potassium carbonate
  9. customAfter the solvent has been evaporated off

Sources & evidence

ORD record
ord-4bebe7f8e81e4f90b2885775fa1b3f5d
Source dataset
uspto-grants-1991_04
Patent number
US05004748

Reaction notes

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