Acetone → 2-Bromo-1-thiophen-3-yl-butan-1-one

HRID 2266170

반응식

HRID 2266170 반응식
CC[Mg+].[Br-].C[C:6]([OH:9])(C)C.[CH3:10][C:11]([CH3:13])=[O:12].[Br:14][CH:15]([CH2:23][CH3:24])[C:16]([C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)=[O:17]>C1C=CC=CC=1>[Br:14][CH:15]([CH2:23][CH3:24])[C:16]([C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)=[O:17].[S:20]1[CH:21]=[CH:22][C:18]([CH:16]([CH2:15][CH3:23])[C:6](=[O:9])[CH2:10][C:11](=[O:12])[CH3:13])=[CH:19]1

참가 물질

7

반응물 4

HCID 180Acetone2회HCID 6386tert-ButanolHCID 595986182-Bromo-1-thiophen-3-yl-butan-1-oneHCID 178461630HCID 178461630, 화합물

생성물 2

HCID 595986182-Bromo-1-thiophen-3-yl-butan-1-oneHCID 595986385-Thiophen-3-yl-heptane-2,4-dione

시약·촉매·용매 1

HCID 241Benzene용매2회

반응 조건

온도
0 °C

실험 절차

EtMgBr (6.69 ml, 13 mmol, 2 M in ethyl ether) in benzene (10 ml) was cooled to zero degrees C, and tBuOH (1.28 ml, 13 mmol) was slowly added. The reaction mixture was stirred at zero degrees C for 5 minutes, then acetone (530 ul, 7 mmol) was added, followed by a solution of 2-Bromo-1-thiophen-3-yl-butan-1-one (1.3 g, 6 mmol) in 3 ml benzene via cannula. The reaction mixture was heated to reflux for 1 hour, and acetone (250 ul) was added. The reaction mixture was heated 2 hours more at reflux. The reaction was cooled, quenched with 1 N HCl (10 ml), extracted three times with diethyl ether, washed brine, and dried over magnesium sulfate. The solvent was removed in vacuo and the residue chromatographed (5% ethyl acetate/hexanes) to give 247 mg of 2-Bromo-1-thiophen-3-yl-butan-1-one starting material and 520 mg of 5-Thiophen-3-yl-heptane-2,4-dione, 44% .

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureThe reaction mixture was heated 2 hours more
  4. temperatureat reflux
  5. temperatureThe reaction was cooled
  6. customquenched with 1 N HCl (10 ml)
  7. extractionextracted three times with diethyl ether
  8. washwashed brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was removed in vacuo
  11. customthe residue chromatographed (5% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-ccbfb89603834a1a90ac0f1bafeaa854
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858632B2

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