Diisopropylamine → 3,3-Bis(3-fluorophenyl)-2-propenal

HRID 2232733Notes

Reaction equation

HRID 2232733 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)=O.C(NC(C)C)(C)C.C([Li])CCC.ClP(=O)(OCC)[O:31][CH2:32][CH3:33]>CCCCCC.C(N=CC)(C)(C)C.O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=2)=[CH:33][CH:32]=[O:31])[CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 7912DiisopropylamineHCID 13139Diethyl chlorophosphateHCID 5795023,3'-DifluorobenzophenoneHCID 178418339Butyllithium

Product 1

HCID 143472293,3-Bis(3-fluorophenyl)-2-propenal

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 138901N-Ethylidene-2-methylpropan-2-amineSolvent

Procedure

The compound was prepared according to the procedure described in Example 84. The following reagents were used: 3,3'-difluorobenzophenone (19.8 g), diisopropylamine (32.2 mL), 1.55M n-butyl lithium in hexane (148 mL), acetaldehyde N-tertbutylimine (14.75 mL), diethyl chlorophosphonate (16.6 mL) and tetrahydrofurane (200 mL). The usual work up gave 23 g of material which was crystallized from hexane to give 17.4 g of 3,3-bis(3-fluorophenyl)-2-propenal, mp 51°-53° C. A small portion was recrystallized from the same solvent to provide the analytical sample, mp 52°-54° C.

Workup

  1. customThe compound was prepared
  2. customThe usual work up gave 23 g of material which was crystallized from hexane

Sources & evidence

ORD record
ord-7930471fe9304334867c46d4d75d7837
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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