Propargyl alcohol → HCID 131716819, compound

HRID 1084335Notes

Reaction equation

HRID 1084335 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.[CH2:16]([OH:19])[C:17]#[CH:18]>C(Cl)Cl>[OH:19][CH2:16][C:17]#[C:18][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 7859Propargyl alcoholHCID 14256374HCID 14256374, compound

Product 1

HCID 131716819HCID 131716819, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg of dimethyl 5-bromodicarboxylate (from Example 3) and 121 mg of propargyl alcohol are dissolved in methylene chloride in a flask flushed with argon, and 840 μl of triethylamine are added dropwise. The mixture is stirred at room temperature for 15 minutes, 25 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added and the mixture is boiled under reflux for 30 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 evaporation and chromatography on silica gel, 260 mg of a white solid remain.

Workup

  1. customflushed with argon, and 840 μl of triethylamine
  2. additionare added dropwise
  3. addition25 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added
  4. temperatureunder reflux for 30 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 evaporation and chromatography on silica gel, 260 mg of a white solid

Sources & evidence

ORD record
ord-b8ca3c3ffcdd433087fb990a49c6899d
Source dataset
uspto-grants-1991_04
Patent number
US05004748

Reaction notes

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