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4,4'-Difluorobenzophenone → HCID 15133036, compound

HRID 1086066
Notes
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Reaction equation

HRID 1086066 reaction equation
C([N-]C(C)C)(C)C.[Li+].[CH:9]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[F:21][C:22]1[CH:36]=[CH:35][C:25]([C:26]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1>O1CCCC1>[CH:9]1([CH:15]([C:26]([C:25]2[CH:35]=[CH:36][C:22]([F:21])=[CH:23][CH:24]=2)([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[OH:27])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 95824,4'-DifluorobenzophenoneHCID 21595Ethyl cyclohexylacetateHCID 2724682Lithium diisopropylamide

Product 1

HCID 15133036HCID 15133036, compoundYield 813.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

Lithium diisopropylamide (56 mL of 1.8M, 100 mmol) was added to a solution of ethyl cyclohexylacetate (16.0 g, 100 mmol) in 50 mL tetrahydrofuran at -40° C. and the solution stirred for 0.5 hour. After further cooling to -70° C., 4,4'-difluorobenzophenone (10.9 g, 50 mmol) was added and the solution stirred for 1 hour at -70° C. and then allowed to warm to -10° C. during the next 2 hrs. The reaction was quenched with 2N hydrochloric acid and extracted with diethyl ether. The extracts were dried with magnesium sulfate and concentrated in vacuo. The residue was crystallized from hexane to give 158 g of the title compound; m.p. =118°-119° C.

Workup

  1. stirringthe solution stirred for 1 hour at -70° C.
  2. temperatureto warm to -10° C. during the next 2 hrs
  3. customThe reaction was quenched with 2N hydrochloric acid
  4. extractionextracted with diethyl ether
  5. dry with materialThe extracts were dried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from hexane

Sources & evidence

ORD record
ord-2b288c349c0c4762a78acacfe52bfd21
Source dataset
uspto-grants-1991_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05011947

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes