Propargyl alcohol → HCID 56976693, compound

HRID 354089Notes

Reaction equation

HRID 354089 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[C:11]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:12]=3[S:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:36]([OH:39])[C:37]#[CH:38]>O.[Cu]I.[Cu](I)I>[OH:39][CH2:36][C:37]#[C:38][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[C:11]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:12]=3[S:13][C:14]=2[C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[O:9])=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 23512917HCID 23512917, compound

Product 1

HCID 56976693HCID 56976693, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 83717Copper iodideCatalystHCID 962WaterSolvent

Procedure

The product from Step 1 (214 mg, 0.43 mmol) was combined with triethylamine (35 mL), copper (I) iodide (0.4 mg), propargyl alcohol (50 mL, 0.86 mmol), bis-triphenylphosphine palladium dichloride at room temperature. The copper iodide was added last. The reaction was stirred for 3 hours then diluted with water and extracted into methylene chloride. The combined organic layers was dried over anhydrous magnesium sulfate. After filtration, concentration and silica gel column chromatography with 1.5% methanol-methylene chloride (gravity column) as eluant the title compound (195 mg) was obtained.

Workup

  1. extractionextracted into methylene chloride
  2. dry with materialThe combined organic layers was dried over anhydrous magnesium sulfate
  3. filtrationAfter filtration, concentration and silica gel column chromatography with 1.5% methanol-methylene chloride (gravity column) as eluant the title compound (195 mg)
  4. customwas obtained

Sources & evidence

ORD record
ord-64268652ef2c483a959966f4c467bcb0
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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