Sodium Iodide → HCID 53788388, 화합물

HRID 1432883노트

반응식

HRID 1432883 반응식
C([O-])(O)=O.[Na+].[Na+].[I-].Br[C:9]1[S:13][C:12]([Cl:14])=[CH:11][CH:10]=1.[CH2:15]([OH:18])[CH:16]=[CH2:17]>CN(P(N(C)C)(N(C)C)=O)C.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:14][C:12]1[S:13][C:9]([CH2:17][CH2:16][CH:15]=[O:18])=[CH:10][CH:11]=1

참가 물질

8

반응물 4

HCID 5238Sodium IodideHCID 7858Allyl AlcoholHCID 761332-Bromo-5-chlorothiopheneHCID 516892Sodium Bicarbonate

생성물 1

HCID 53788388HCID 53788388, 화합물수율 20.4%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매HCID 12679Hexamethylphosphoramide용매

반응 조건

온도
90 °C

실험 절차

To a mixture of Pd(OAc)2 (0.12 g, 0.53 mmol), NaHCO3 (0.52 g, 6.19 mmol) and NaI (0.28 g, 1.87 mmol) in 5 mL of HMPA is added 5-bromo-2-chloro-thiophene (1.00 g, 5.06 mmol) and allyl alcohol (1.03 mL, 15.2 mmol). The mixture is heated to 90° C. and stirred for 16 hours. The reaction mixture is cooled to room temperature, diluted with Et2O and washed with water. The organic layer is dried over MgSO4, filtered and concentrated in vacuo. The crude residue is purified by flash column chromatography eluting with a gradient of 10% Et2O/hexanes to 20% Et2O/hexanes to provide the product (0.18 g, 1.03 mmol) as an oil. 1H NMR (CDCl3, 300 MHz) δ9.81 (s, 1H), 6.71 (d, 1H), 6.58 (d, 1H), 3.07 (t, 2H), 2.81 (t, 2H).

후처리

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue is purified by flash column chromatography
  7. washeluting with a gradient of 10% Et2O/hexanes to 20% Et2O/hexanes

출처 및 근거

ORD 기록
ord-3a62767deb3a4916a6a8a10d3e00875f
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612075B2

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