Water → 3-(Benzyloxy)cyclobutan-1-one

HRID 1009160

반응식

HRID 1009160 반응식
CS(CSC)=[O:3].[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].BrCC(O[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)CBr.[OH2:25]>C1COCC1>[CH2:18]([O:25][CH:8]1[CH2:9][C:10](=[O:3])[CH2:7]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 561824(((1,3-Dibromopropan-2-yl)oxy)methyl)benzeneHCID 178418339Butyllithium

생성물 1

HCID 149327873-(Benzyloxy)cyclobutan-1-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-20 °C

실험 절차

Methylsulfinyl(methylthio)methane (13 ml, 125 mmol) was dissolved in 250 ml THF and cooled to −20° C. n-Butyllithium (50 ml, 125 mmol) was added and the mixture was stirred for 3 h at −20° C. The mixture was cooled down to −78° C. and a solution of 1-((1,3-dibromopropan-2-yloxy)methyl)benzene (16.000 g, 52 mmol) was added. The reaction was stirred over night and allowed to warm up to RT. It was stirred for an additional 6 h at RT, hydrolyzed with water and extracted with EtOAc. The combined organic extracts were evaporated, dissolved in ether (50 ml) and treated with conc. HCl (10 ml) for 30 min at reflux. The mixture was neutralized with NaOH (10M) and extracted with EtOAc. The combined organic extracts were dried over MgSO4 and evaporated. Glass col. Chrom. (10-50% EtOAc in Hex) gave 3-(benzyloxy)cyclobutanone as a yellow oil.

후처리

  1. additionwas added
  2. temperatureThe mixture was cooled down to −78° C.
  3. stirringThe reaction was stirred over night
  4. temperatureto warm up to RT
  5. extractionextracted with EtOAc
  6. customThe combined organic extracts were evaporated
  7. dissolutiondissolved in ether (50 ml)
  8. additiontreated with conc. HCl (10 ml) for 30 min
  9. temperatureat reflux
  10. extractionextracted with EtOAc
  11. dry with materialThe combined organic extracts were dried over MgSO4
  12. customevaporated

출처 및 근거

ORD 기록
ord-62640e8f36fa48219755166f11fe779e
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973047B2

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