Benzophenone → HCID 58225130, compound

HRID 713549Notes

Reaction equation

HRID 713549 reaction equation
Br[C:2]12[CH:9]=[CH:8][CH:7]=[CH:6][CH:3]1[CH2:4][CH2:5]2.C([Li])CCC.[C:15]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[CH2:5]1[C:2]2[CH:9]=[CH:8][C:7]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[OH:22])=[CH:6][C:3]=2[CH2:4]1

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 131734053HCID 131734053, compoundHCID 178418339Butyllithium

Product 1

HCID 58225130HCID 58225130, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-bromobenzocylcobutene (1.5 g, 8.2 mmol) was dissolved in 50 ml of THF. The solution was cooled to −78° C. To the solution was added butyl-lithium (3.6 mL, 2.0 M in hexanes, 9.0 mmol). After 45 minutes, benzophenone (1.34 g, 7.4 mmol) was added in one portion. The reaction was allowed to warm to room temperature overnight. After normal work-up, the residue was purified by column using 1:1 dichloromethane and hexanes as solvent. 0.9 g of the desired product was obtained (42% yield).

Workup

  1. temperatureto warm to room temperature overnight
  2. customAfter normal work-up, the residue was purified by column

Sources & evidence

ORD record
ord-3ee6e994855e4a51a802e3d9c9b7338d
Source dataset
uspto-grants-2015_11
Patent number
US09184394B2

Reaction notes

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