Diethyl Ether → HCID 57425853, compound

HRID 1727319Notes

Reaction equation

HRID 1727319 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:14][C:13](=[O:15])[C:12]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][CH2:10][CH:11]1[CH2:12][C:13](=[O:15])[CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 57425854HCID 57425854, compound

Product 1

HCID 57425853HCID 57425853, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Zinc dust was added to a solution of 3-(benzyloxyethyl)-2,2-dichlorocyclobutanone in glacial acetic acid 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 CH2Cl2, 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 silica gel flash chromatography (Hexane:EtOAc=6:1). 1H NMR (CDCl3, 400 MHz): δ 1.85-1.90 (q, J=6.0, 2H), 2.45-2.56 (m, 1H), 2.66-2.74 (m, 2H), 3.07-3.15 (m, 2H), 3.48-3.51 (t, J=6.0, 2H), 4.48 (s, 2H), 7.24-7.35 (m, 5H). 13C NMR (CDCl3, 100 MHz): δ 21.29, 36.02, 52.56, 68.85, 72.99, 127.56, 127.62, 128.40, 138.33, 208.25. Rf=0.45 (Hexane:EtOAc=3:1). IR (neat) νmax 3054, 2927, 2856, 1779, 1266, 737, 704.

Workup

  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 CH2Cl2
  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 silica gel flash chromatography (Hexane:EtOAc=6:1)

Sources & evidence

ORD record
ord-b1a04992c5844d02bc2ca1305f79673d
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

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