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Iodoethane → HCID 86705340, 화합물

HRID 587986
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HRID 587986 반응식
[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][CH:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:15][CH3:16])=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].O1CC[CH2:39][CH2:38]1.C(I)C>O1CCCC1>[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH2:13][C:14]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])([CH2:38][CH3:39])[CH2:15][CH3:16])=[CH:11][CH:12]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 23714775LiHMDS tetrahydrofuranHCID 86705338HCID 86705338, 화합물

생성물 1

HCID 86705340HCID 86705340, 화합물수율 78.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-(2-Benzyloxycarbonylbutyl)thiophene-2-carboxylic acid tert-butyl ester (29.5 g, 78.8 mmol) was dissolved in tetrahydrofuran (200 mL), 1.09 M lithium bis(trimethylsilyl)azanide/tetrahydrofuran solution (94 mL, 102 mmol) was added dropwise at −78° C., and the mixture was stirred for 2 hours. To the reaction mixture was added ethyl iodide (12.3 g, 156 mmol) at −78° C., and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was added to ethyl acetate and 0.5 N-hydrochloric acid solution, the organic layer was separated, and the aqueous layer was extracted two times with ethyl acetate. The organic layers were combined, washed with sodium thiosulfate solution and brine, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (24.9 g, 61.9 mmol, 78%).

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was added to ethyl acetate and 0.5 N-hydrochloric acid solution
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted two times with ethyl acetate
  6. washwashed with sodium thiosulfate solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b6970b3d29de43cdbd3d28e18fc79b9c
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09227949B2

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