Water → HCID 178454983, compound

HRID 1901771Notes

Reaction equation

HRID 1901771 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1OCC(O)C#C.I[C:14]1[S:18][C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:15]=1.[OH-:24].[Na+].[NH4+].[Cl-].[OH2:28]>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:24][C:5]1[CH2:6][O:1][CH:2]=[CH:3][C:4]=1[O:28][C:14]1[SH:18]([C:2]#[C:3][CH2:4][CH3:5])[C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:16][CH:15]=1

Participants

10

Reactant 5

HCID 962WaterHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 113237785-Iodo-2,2'-bithiopheneHCID 18920430HCID 18920430, compound

Product 1

HCID 178454983HCID 178454983, compoundYield 95%

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

4-(Tetrahydropyranyloxy)-3-hydroxy-butyne (6.7 g) was dissolved in benzene (20 ml). 5-Iodo-2.2'-bithiophene (5.75 g) was added immediately and stirred. A mixture of CuI (0.15 g) and benzyltriethylammonium chloride (0.14 g, 0.63 mmole) was added. Pd(PPh3)4 (0.46 g, 0.398 mmole) was then added. NaOH solution (30 ml, 2.5N) was added slowly into the mixture at room temperature in water bath for 2 hours. NH4Cl solution (10 ml) was 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 for 3 times and dried over anhydrous magnesium sulfate. The residual solid after evaporation was purified by silica gel column chromatography, eluted with ethyl acetate/n-hexane (1/3). Reddish oily product (6.25 g, 95%) was then obtained.

Workup

  1. additionwas added
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washThe extract was washed with 10 ml of HCl (10%) for 3 times, 50 ml of water for 3 times
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residual solid after evaporation
  6. customwas purified by silica gel column chromatography
  7. washeluted with ethyl acetate/n-hexane (1/3)

Sources & evidence

ORD record
ord-f36dfdc29fca46f5ac615b68cd9b8f6e
Source dataset
uspto-grants-1996_11
Patent number
US05578636

Reaction notes

Loading…