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

HRID 1727304

反応式

HRID 1727304 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 118198503-((Benzyloxy)methyl)cyclobutanone

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f3009f36b5074d57a6c22dfb2f4b640e
出典データセット
uspto-grants-2009_02
特許番号
US07495006B2

関連ノート

読み込み中…