4,4'-Difluorobenzophenone → HCID 15133039, compound

HRID 1086078Notes

Reaction equation

HRID 1086078 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH3:9][C:10]([CH3:18])([CH3:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[F:19][C:20]1[CH:34]=[CH:33][C:23]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)=[O:25])=[CH:22][CH:21]=1>O1CCCC1>[F:19][C:20]1[CH:34]=[CH:33][C:23]([C:24]([C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=2)([OH:25])[CH:11]([C:10]([CH3:18])([CH3:17])[CH3:9])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 95824,4'-DifluorobenzophenoneHCID 79284Ethyl 3,3-dimethylbutyrateHCID 2724682Lithium diisopropylamide

Product 1

HCID 15133039HCID 15133039, compoundYield 627.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

Lithium diisopropylamide (21.7 mL of 1.8M solution, 40 mmol) was added to a solution of ethyl 3,3-dimethylbutyrate (5.76 g, 40 mmol) in 40 mL of tetrahydrofuran at -35° C. After stirring for 30 minutes and further cooling to -50° C., 4,4'-difluorobenzophenone (4.36 g, 2 mmol) was added. The reaction was stirred for 2 hours at -50° and for 2 hours at -20° C. The mixture was quenched with 2N hydrochloric acid and extracted with diethyl ether. The extracts were dried and concentrated in vacuo. The residue was crystallized from petroleum ether to give 4.55 g of the title compound; m.p. =93°-96° C.

Workup

  1. stirringThe reaction was stirred for 2 hours at -50° and for 2 hours at -20° C
  2. customThe mixture was quenched with 2N hydrochloric acid
  3. extractionextracted with diethyl ether
  4. customThe extracts were dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from petroleum ether

Sources & evidence

ORD record
ord-b40c6466c53c4ec4b3b559a09f76a825
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

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