Sodium Hydroxide → 5-(3-Hydroxy-1-propynyl)-2,2'-bithiophene

HRID 1901766Notes

Reaction equation

HRID 1901766 reaction equation
[OH:1][C:2]#[C:3][CH3:4].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-]>C1C=CC=CC=1.[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>[OH:1][CH2:2][C:3]#[C:4][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 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 6432594Prop-1-yn-1-olHCID 113237785-Iodo-2,2'-bithiophene

Product 1

HCID 189204415-(3-Hydroxy-1-propynyl)-2,2'-bithiopheneYield 74.3%

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

Hydroxy-1-propyne (48 mg) was dissolved in benzene (1 ml). 5-Iodo-2,2'-bithiophene (0.1 g) was added immediately and stirred. A mixture of CuI (0.05 g), benzyltriethylammonium chloride (0.05 g), catalyst Pd(PPh3)4 (0.1 g) and 3 ml of NaOH solution (2.5N) were mixed together at room temperature and stirred for 2 hours. NH4Cl solution (4 ml) was then added. The reaction solution was extracted with 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, eluted with ethyl acetate/n-hexane (3/1) to yield 56 mg of the product (74% ).

Workup

  1. additionwere mixed together at room temperature
  2. stirringstirred for 2 hours
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. washThe extract was washed with 10 ml of HCl (10%) for 3 times, 50 ml of water twice
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe residual solid was purified by silica gel column chromatography
  7. washeluted with ethyl acetate/n-hexane (3/1)

Sources & evidence

ORD record
ord-8894311ad013430c888ea0e172e2dce2
Source dataset
uspto-grants-1996_11
Patent number
US05578636

Reaction notes

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