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

HRID 1110490Notes

Reaction equation

HRID 1110490 reaction equation
[Cl: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]([Cl: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>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([Cl: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 3483033,3'-DichlorobenzophenoneHCID 178418339Butyllithium

Product 1

HCID 145472273,3-Bis(3-chlorophenyl)-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'-dichlorobenzophenone (25.1 g), diisopropylamine (32.2 mL), 1.6M n-butyl lithium in hexane (144 mL), acetaldehye N-tert-butylimine (14.75 mL), diethyl chlorophosphonate (16.6 mL) and tetrahydrofurane (200 mL). The usual work up furnished 24.0 g of essentially pure 3,3-bis(3-chlorophenyl)-2-propenal as an orange oil.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-faa7f035b67e47a6a2a938ac38baa790
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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