1-Cyclobutylethan-1-one → HCID 67375753, compound

HRID 401987Notes

Reaction equation

HRID 401987 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH:15]1([C:19]([CH3:21])=[O:20])[CH2:18][CH2:17][CH2:16]1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:15]1([C:19](=[O:20])[CH2:21][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]3)=[CH:4][CH:3]=2)[CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 763981-Cyclobutylethan-1-oneHCID 634876Binap, (A+-)-HCID 111397141-Bromo-4-(cyclohexyloxy)benzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 67375753HCID 67375753, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
130 °C

Procedure

A stirred suspension of 1-bromo-4-cyclohexyloxy-benzene (Example 60, 4.18 mmol, 1.05 g), cyclobutylmethylketone (5.23 mmol, 0.57 mL), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.50 mmol, 0.31 g), tris(dibenzylideneacetone)dipalladium(0) (0.21 mmol, 0.19 g), and potassium t-butoxide (6.27 mmol, 0.70 g) was heated in a single mode microwave synthesizer to 130° C. for 1 h in a 10 mL microwave sealed tube. The reaction was cooled and partitioned in water (20 mL) and diethyl ether (50 mL). The mixture was filtered through fluted filter paper and the layers were separated. The aqueous layer was washed with diethyl ether (50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified on 2×40 g SiO2 cartridges stacked using a 0-20% ethyl acetate/hexanes gradient to give 1-cyclobutyl-2-(4-cyclohexyloxy-phenyl)-ethanone (0.98 g).

Workup

  1. customsealed tube
  2. temperatureThe reaction was cooled
  3. custompartitioned in water (20 mL)
  4. filtrationThe mixture was filtered
  5. filtrationthrough fluted filter paper
  6. customthe layers were separated
  7. washThe aqueous layer was washed with diethyl ether (50 mL)
  8. dry with materialThe combined organic layers were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified on 2×40 g SiO2 cartridges

Sources & evidence

ORD record
ord-2190a07b41854a5089c0affebdb66d23
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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