1,2-Dimethoxyethane → HCID 23365812, 화합물

HRID 129513

반응식

HRID 129513 반응식
COCCOC.I[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:10][C:9]=1[NH2:19].[CH3:20][Si:21]([C:24]#[C:25][Si](C)(C)C)([CH3:23])[CH3:22].C([O-])([O-])=O.[Na+].[Na+]>CCCCCC.CCOC(C)=O.CO>[CH3:18][S:15]([CH2:14][C:12]1[CH:13]=[C:8]2[C:9](=[CH:10][CH:11]=1)[NH:19][C:24]([Si:21]([CH3:23])([CH3:22])[CH3:20])=[CH:25]2)(=[O:17])=[O:16]

참가 물질

8

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 84564Bis(trimethylsilyl)acetyleneHCID 193717842-Iodo-4-[(methylsulfonyl)methyl]benzenamine

생성물 1

HCID 23365812HCID 23365812, 화합물수율 83%

시약·촉매·용매 3

HCID 887Methanol용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of 1,2-dimethoxyethane (DME, 70 mL) was added 2 -iodo-4-[(methylsulfonyl)methyl]benzenamine (1) (1.9 g, 0.0061 mol), bis(trimethylsilyl) acetylene (1.56 g, 0.00915 mol), tetrakistriphenylphosphine Pd(O) (0.705 g, 0.00061 mol) and saturated aqueous Na2CO3 (5 mL). The reaction was heated at reflux for 48 h. The solvent was removed in vacuo and the residue was dissolved in EtOAc and washed with brine. The organic layer was dried over MgSO4, filtered and evaporated to give the crude product. Silica gel chromatography (20-100% EtOAc gradient in hexane followed by 5-10% MeOH gradient in EtOAc) of the concentrate afforded the product (2) (1.42 g, 83%) as a brown oil.

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 48 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give the crude product

출처 및 근거

ORD 기록
ord-4886fc6c00284f27b3cec637fc1a9d33
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468768

연결된 노트

불러오는 중…