1-(Carboethoxy)methyliminomethyl-3,4-dimethoxybenzene → N-[1-carboethoxy-5-(3,4-dimethoxyphenyl)-5-cyano-5-(isopropyl)pentyl]iminomethyl-3,4-dimethoxybenzene
Reaction equation
[C:1]([CH2:6][N:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)([O:3][CH2:4][CH3:5])=[O:2].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:29]([CH:36]([CH3:38])[CH3:37])([CH2:32][CH2:33][CH2:34]I)[C:30]#[N:31])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>>[C:1]([CH:6]([N:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:34][CH2:33][CH2:32][C:29]([C:23]1[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:21]([O:20][CH3:19])[CH:22]=1)([C:30]#[N:31])[CH:36]([CH3:38])[CH3:37])([O:3][CH2:4][CH3:5])=[O:2]Participants
3
Procedure
The resulting imine of formula 24 is then deprotonated using a suitable strong base, and allowed to react with a compound of formula 22 to produce a compound of formula 25 (step 2). For example, 1-(carboethoxy)methyliminomethyl-3,4-dimethoxybenzene (24) is suspended in a solution of LiNiPr2 in THF/HMPA at -78° C., then reacted with 2-(3,4-dimethoxyphenyl)-2-isopropyl-2-(3-iodopropyl)acetonitrile (22) to produce N-[1-carboethoxy-5-(3,4-dimethoxyphenyl)-5-cyano-5-(isopropyl)pentyl]iminomethyl-3,4-dimethoxybenzene (25).
Sources & evidence
- ORD record
- ord-7c71cf0b7d6a449ea49aefe9390e35f4
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04667038
Reaction notes
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