Diethyl Ether → HCID 123446256, compound

HRID 1641513Notes

Reaction equation

HRID 1641513 reaction equation
[C:1]([CH:5]([CH:21]1[CH2:24][C:23](=[O:25])[C:22]1(Cl)Cl)[C:6]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[O:7][SiH3:8])([CH3:4])([CH3:3])[CH3:2].C(OCC)C>C(O)(=O)C.[Zn]>[C:1]([CH:5]([CH:21]1[CH2:22][C:23](=[O:25])[CH2:24]1)[C:6]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[O:7][SiH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 124009734HCID 124009734, compound

Product 1

HCID 123446256HCID 123446256, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Zinc dust (15.7 g, 0.24 mol) was added to a solution of 3-(tert-butyl-diphenyl-siloxyethyl)-2,2-dichlorocyclobutanone (17 g, 0.04 mol) in glacial acetic acid (68 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 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=12:1) to give a colorless oil (6.2 g, 43.7%). 1H NMR (CDCl3, 400 MHz): δ 1.06 (s, 9H), 1.82-1.87 (m, 2H), 2.48-2.60 (m, 1H), 2.65-2.71 (m, 2H), 3.07-3.14 (m, 2H), 3.69-3.73 (t, J=6.0, 6.4, 2H), 7.37-7.46 (m, 6H), 7.65-7.73 (m, 4H). 13C NMR (CDCl3, 100 MHz): δ 19.37, 26.76, 27.06, 39.02, 52.87, 62.87, 127.91, 129.88, 129.92, 133.86, 208.89. IR (neat) νmax 2957, 2930, 2857, 1784, 1472, 1428, 1388, 1112, 822, 739, 702.

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=12:1)

Sources & evidence

ORD record
ord-0a726b7693664571bbe52815df2cf7e7
Source dataset
uspto-grants-2012_02
Patent number
US08114994B2

Reaction notes

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