Propargyl alcohol → 5-(3-Hydroxy-1-propynyl)-2,2'-bithiophene

HRID 1291597Notes

Reaction equation

HRID 1291597 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].I[C:6]1[S:10][C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:7]=1.[OH-].[Na+].[NH4+].[Cl-]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC=CC=1>[OH:4][CH2:1][C:2]#[C:3][C:6]1[S:10][C:9]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:7]=1

Participants

9

Reactant 4

HCID 7859Propargyl alcoholHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 113237785-Iodo-2,2'-bithiophene

Product 1

HCID 189204415-(3-Hydroxy-1-propynyl)-2,2'-bithiopheneYield 74%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 66133Benzyl triethylammonium chlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolvent

Procedure

To the mixture of 48 mg (0.86 mmole) of propargyl alcohol, 1 ml of benzene, 0.1 g of 5-iodo-2,2'-bithiophene (0.34 mmole) was added 0.25 g of CuI, 0.05 g of benzyltriethylammonium chloride and 0.1 g of Pd(PPh3)4. To the solution, 3 ml of NaOH solution (2.5 N) was added at room temperature and stirred for 2 hours. 4 ml of NH4Cl solution was then added. The reaction solution was extracted with 50 ml of ethyl acetate. The extract was washed with 10 ml of HCl (10%) for 3 times, 50 ml of water twice and dried over anhydrous magnesium sulfate. The residual solid was purified by silica gel column chromatography. From the eluate of ethyl acetate/n-hexane (3/1) 56 mg of product (74%) was obtained.

Workup

  1. extractionThe reaction solution was extracted with 50 ml of ethyl acetate
  2. washThe extract was washed with 10 ml of HCl (10%) for 3 times, 50 ml of water twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe residual solid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6d87f343c025411bb1f67f975173002c
Source dataset
uspto-grants-1998_05
Patent number
US05753692

Reaction notes

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