3-Phenylcyclobutanone → (3-Methylidenecyclobutyl)benzene

HRID 1280748Notes

Reaction equation

HRID 1280748 reaction equation
[Li][CH2:2]CCC.[C:6]1([CH:12]2[CH2:15][C:14](=O)[CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.CCCCCC>[CH2:2]=[C:14]1[CH2:15][CH:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:13]1

Participants

6

Reactant 2

HCID 1429633-PhenylcyclobutanoneHCID 178418339Butyllithium

Product 1

HCID 18425796(3-Methylidenecyclobutyl)benzeneYield 40%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 2-3° C. suspension of methyltriphenylphosphonium bromide (0.36 g, 1 mmol) in THF (2.5 ml) was added dropwise n-BuLi (0.69 ml, 1.1 mmol, 1.6 M in hexan). After 1 hour stirring at 0° C., a solution of 3-phenyl-cyclobutanone (0.146 g, 1 mmol) in THF (1.5 ml) was added dropwise. The reaction mixture was stirred 24 hours at room temperature and then diluted with hexane. The so obtained precipitate was filtered and the filtrate was concentrated. The residue was chromatographed over silica gel (hexane-ethylacetate 9:1) to provide (3-methylene-cyclobutyl)-benzene (57 mg, 40%) as a slightly yellow oil, MS: m/e=144.1 (M+).

Workup

  1. stirringThe reaction mixture was stirred 24 hours at room temperature
  2. customThe so obtained precipitate
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was chromatographed over silica gel (hexane-ethylacetate 9:1)

Sources & evidence

ORD record
ord-c794459388454186accc6ca607f1adac
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

Loading…