Water → HCID 178454983、化合物

HRID 1901771ノート

反応式

HRID 1901771 の反応式
[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

参加物

10

反応物 5

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

生成物 1

HCID 178454983HCID 178454983、化合物収率 95%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 66133Benzyl triethylammonium chloride触媒HCID 178418397HCID 178418397、化合物触媒HCID 241Benzene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f36dfdc29fca46f5ac615b68cd9b8f6e
出典データセット
uspto-grants-1996_11
特許番号
US05578636

反応ノート

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