Methyl 4-pentynoate → HCID 131716818, compound

HRID 1084334Notes

Reaction equation

HRID 1084334 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.[C:16]([O:22][CH3:23])(=[O:21])[CH2:17][CH2:18][C:19]#[CH:20]>C(Cl)Cl>[CH3:23][O:22][C: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)=[O:21]

Participants

4

Reactant 2

HCID 543061Methyl 4-pentynoateHCID 14256374HCID 14256374, compound

Product 1

HCID 131716818HCID 131716818, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

546 mg of dimethyl 5-bromo-dicarboxylate (from Example 3) and 269 mg of methyl 4-pentinoate 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, 28 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added and the mixture is boiled under reflux for 18 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, 460 mg of a white solid remain.

Workup

  1. customflushed with argon, and 840 μl of triethylamine
  2. additionare added dropwise
  3. addition28 mg of ((C6H5)3P)2PdCl2 and 4 mg of CuI are added
  4. temperatureunder reflux for 18 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, 460 mg of a white solid

Sources & evidence

ORD record
ord-c11aeeaec7054079b5c194ce839e3b6a
Source dataset
uspto-grants-1991_04
Patent number
US05004748

Reaction notes

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