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

HRID 1291598Notes

Reaction equation

HRID 1291598 reaction equation
[OH:1][CH:2]([CH3:5])[C:3]#[CH:4].I[C:7]1[S:11][C:10]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[CH:9][CH:8]=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:1][CH:2]([CH3:5])[C:3]#[C:4][C:7]1[S:11][C:10]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[CH:9][CH:8]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 162393-Butyn-2-olHCID 25517Ammonium ChlorideHCID 113237785-Iodo-2,2'-bithiophene

Product 1

HCID 189204265-(3-Hydroxy-1-butynyl)-2,2'-bithiopheneYield 93%

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 1 g (14.3 mmole) of 3-hydroxy-1-butyne, 10 ml of benzene and 2.78 g of 5-iodo-2,2'-bithiophene (9.52 mmole) was added 0.15 g of CuI, 0.15 g of benzyltriethylammonium chloride, 0.2 g of Pd(PPh3)4 and then 15 ml of NaOH solution (2.5 N) at room temperature and stirred for 2 hours. 4 ml of NH4Cl solution 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 crude product was purified by silica gel column chromatography. From the eluate of ethyl acetate/n-hexane (3/1) 2.07 g of yellow solid product (93%) was obtained.

Workup

  1. extractionThe reaction solution was extracted with 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 crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a80f4177b09c4bcc8737a3b69cb47f9b
Source dataset
uspto-grants-1998_05
Patent number
US05753692

Reaction notes

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