1,5-Diphenylpentan-3-one → HCID 21635958, compound

HRID 847587Notes

Reaction equation

HRID 847587 reaction equation
[CH2:1]([Li])CCC.[C:6]1([CH2:12][CH2:13][C:14](=O)[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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.O1CCCC1.CCCCCC>[C:6]1([CH2:12][CH2:13][C:14]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH2:1])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 2

HCID 214961,5-Diphenylpentan-3-oneHCID 178418339Butyllithium

Product 1

HCID 21635958HCID 21635958, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A suspension of 1.59 g (4.45 mmol) of methyltriphenylphosphonium bromide in 100 ml of tetrahydrofuran was cooled to -78° C., treated with 2.2 ml (4.5 mmol) of n-butyllithium, warmed to 0° C, was recooled to -78° C. The resulting solution was treated via cannula with a solution of 1.59 g (4.45 mmol) of 1,5diphenyl-3-pentanone in 20 ml of tetrahydrofuran. After being allowed to stir at ambient temperature for 2 h, the solution was diluted with hexane, washed sequentially with water and saturated brine, dried over MgSO4, and concentrated in vacuo. The mixture was purified by flash chromatography to give 0.90 g (86%) of the desired compound as a colorless oil. 1H NMR (CDCl3) δ 2.37 (t, J=8 Hz, 4H), 2.76 (t, J=8 Hz, 4H), 4.81 (s, 2H), 7.15-7.3 (m, 10H). Mass spectrum (M+NH4)+ =254.

Workup

  1. temperaturewarmed to 0° C
  2. customwas recooled to -78° C
  3. washwashed sequentially with water and saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-46eea8fad22d47698222cb6648d7ad52
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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