Water → HCID 178454983, 화합물

HRID 1901771노트

반응식

HRID 1901771 반응식
[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

참가 물질

10

반응물 5

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

생성물 1

HCID 178454983HCID 178454983, 화합물수율 95%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 66133Benzyl triethylammonium chloride촉매HCID 178418397HCID 178418397, 화합물촉매HCID 241Benzene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f36dfdc29fca46f5ac615b68cd9b8f6e
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05578636

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