Cyclohexane → o-Nitrophenyl cyclopropyl ketone

HRID 342191Notes

Reaction equation

HRID 342191 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:15])[CH2:11][CH2:12][CH2:13]Br)([O-:3])=[O:2].C([N-]C(C)C)(C)C.[Li+].C1CCCCC1.[NH4+].[Cl-]>O1CCCC1>[CH:11]1([C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[O:15])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 537739744-Bromo-2'-nitrobutyrophenone

Product 1

HCID 10487947o-Nitrophenyl cyclopropyl ketoneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1 (o-nitrophenyl)-4-bromo-1-butanone (0.75 g, 2.75 mmol) in dry tetrahydrofuran (THF) under nitrogen is cooled to -78° C. with stirring, cautiously treated with 2.21 ml of 1.5M lithium diisopropylamide (LDA) in cyclohexane (3.3 mmol LDA), held at -78° C. for 1 hour, allowed to warm to 0° C. for 2 hours and poured onto a saturated NH4Cl solution. The resultant mixture is extracted with ethyl acetate. The extracts are combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to give a residue. The residue is purified by flash column chromatography (silica gel; gradient 15%→25% ethyl acetate in hexane as eluent) to give the title product as a yellow oil, 0.34 g, 64% yield, identified by NMR and mass spectral analyses.

Workup

  1. extractionThe resultant mixture is extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. customThe residue is purified by flash column chromatography (silica gel; gradient 15%→25% ethyl acetate in hexane as eluent)

Sources & evidence

ORD record
ord-c38942d0b3a0445ba883b0aaf0c69388
Source dataset
uspto-grants-1999_01
Patent number
US05856576

Reaction notes

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