Cyclohexane → Dibenzhydryl carboxymethylsuccinate
Reaction equation
C1CCCCC1.C([N-]C(C)C)(C)C.[Li+].[C:15]([O:18]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:17])[CH3:16].[C:38]([O:58][CH:59]([C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)(=[O:57])/[CH:39]=[CH:40]\[C:41]([O:43][CH:44]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42]>C(O)(=O)C.O>[C:15]([CH2:16][CH:40]([CH2:39][C:38]([O:58][CH:59]([C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)[C:66]1[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=1)=[O:57])[C:41]([O:43][CH:44]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:42])([OH:18])=[O:17]Participants
7
Procedure
The reaction product obtained by conducting the Michael-addition reaction in the same manner as in Example 116 using 5.7 ml of a 1.5M cyclohexane solution of lithium diisopropylamide, 2.6 g of trityl acetate and 3.2 g of dibenzhydryl maleate, was dissolved in a liquid mixture of 20 ml of acetic acid and 5 ml of water, and the solution was left to stand at room temperature overnight and then evaporated to dryness under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform/methanol=100/1→10/1) to obtain 1.05 g (yield: 29%) of the above-identified compound as white crystalline powder having a melting point of from 105° to 106° C.
Workup
- customThe reaction product obtained
- waitthe solution was left
- customevaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-108a59315e044653b584b263eaa291a3
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05616803
Reaction notes
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