Diethyl Ether → 3-((Benzyloxy)methyl)cyclobutanone

HRID 1727304

반응식

HRID 1727304 반응식
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:13][C:12](=[O:14])[C:11]1(Cl)Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)C>C(O)(=O)C.[Zn]>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:13][C:12](=[O:14])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 3283Diethyl EtherHCID 103551863-(Benzyloxymethyl)-2,2-dichlorocyclobutanone

생성물 1

HCID 118198503-((Benzyloxy)methyl)cyclobutanone

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

반응 조건

온도
60 °C

실험 절차

Zinc dust (93.5 g, 1.44 mol) was added to a solution of 3-(benzyloxymethyl)-2,2-dichlorocyclobutanone (124 g, 0.48 mol) in glacial acetic acid (800 ml) at room temperature. The reactants were heated at 60° C. for 1 hr, after which time dry diethyl ether was added to the cooled products, which were then filtered. The residue was washed with diethyl ether and the combined filtrate and washings were concentrated under reduced pressure. The residue was dissolved in dichloromethane, which was washed with saturated NaHCO3 twice and water once. The organic phase was dried over MgSO4 and the solvent was evaporated to give an oily product, which was purified by column chromatography (Hexane:EtOAc=6:1). 1H NMR (CDCl3, 400 MHz): δ 2.70 (m, 1H), 2.84-2.92 (m, 2H), 3.08-3.18 (m, 2H), 3.59 (d, J=6.4, 2H), 4.56 (s, 2H), 7.28-7.38 (m, 5H). 13C NMR (CDCl3, 100 MHz): δ 23.88, 50.26, 73.11, 73.42, 127.88, 127.99, 128.68, 138.26, 207.22.

후처리

  1. filtrationwere then filtered
  2. washThe residue was washed with diethyl ether
  3. concentrationthe combined filtrate and washings were concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwhich was washed with saturated NaHCO3 twice
  6. dry with materialThe organic phase was dried over MgSO4
  7. customthe solvent was evaporated
  8. customto give an oily product, which
  9. customwas purified by column chromatography (Hexane:EtOAc=6:1)

출처 및 근거

ORD 기록
ord-f3009f36b5074d57a6c22dfb2f4b640e
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495006B2

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