Diethyl Ether → HCID 123713074, compound

HRID 1727329Notes

Reaction equation

HRID 1727329 reaction equation
[CH:1]([CH:4]([CH:14]1[CH2:17][C:16](=[O:18])[C:15]1(Cl)Cl)[C:5]([CH:11]([CH3:13])[CH3:12])([CH:8]([CH3:10])[CH3:9])[O:6][SiH3:7])([CH3:3])[CH3:2].C(OCC)C>C(O)(=O)C.[Zn]>[CH:1]([CH:4]([CH:14]1[CH2:15][C:16](=[O:18])[CH2:17]1)[C:5]([CH:11]([CH3:12])[CH3:13])([CH:8]([CH3:9])[CH3:10])[O:6][SiH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 123401332HCID 123401332, compound

Product 1

HCID 123713074HCID 123713074, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Zinc dust (25.5 g, 0.39 mol) was added to a solution of 3-(triisopropyl -siloxyethyl)-2,2-dichlorocyclobutanone (22.21 g, 65.4 mmol) in glacial acetic acid (110 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 silica gel flash chromatography (Hexane: EtOAc=12:1) to give a colorless oil. 1H NMR (CDCl3, 400 MHz): δ 1.03-1.08 (m, 21H), 1.80-1.85 (m, 2H), 2.49-2.60 (m, 1H), 2.71-2.80 (m, 2H), 3.12-3.21 (m, 2H), 3.74-3.77 (t, J=6.0, 2H). 13C NMR (CDCl3, 100 MHz): δ 12.12, 18.22, 21.38, 39.36, 52.92, 62.37, 209.00. MS (FAB): expected for C15H30O2Si (M+H)+ 271.48. Found 271.20887. IR (neat) νmax 3053, 2925, 2866, 1778, 1462, 1265, 1103, 1013, 883, 740, 705.

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 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 silica gel flash chromatography (Hexane: EtOAc=12:1)
  10. customto give a colorless oil

Sources & evidence

ORD record
ord-838c9624f3594320996b6d7cdb0d8041
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

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