Toluene → HCID 19755396, compound

HRID 1588435Notes

Reaction equation

HRID 1588435 reaction equation
[CH2:1]([C:4]1[C:16]([O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=2)=[CH:15][CH:14]=[C:13]2[C:5]=1[C:6]1[CH2:7][CH2:8][CH2:9][CH:10]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:11]=1[NH:12]2)[CH:2]=[CH2:3].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C1(C)C=CC=CC=1.[Cl:52][C:53]1[CH:60]=[CH:59][C:56]([CH2:57]Br)=[CH:55][CH:54]=1.[NH4+].[Cl-]>C1COCC1.CN(C)P(N(C)C)(N(C)C)=O>[Cl:52][C:53]1[CH:60]=[CH:59][C:56]([CH2:57][N:12]2[C:11]3[CH:10]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:9][CH2:8][CH2:7][C:6]=3[C:5]3[C:13]2=[CH:14][CH:15]=[C:16]([O:17][CH2:18][C:19]2[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=2)[C:4]=3[CH2:1][CH:2]=[CH2:3])=[CH:55][CH:54]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 2733832Lithium HexamethyldisilazideHCID 19755383HCID 19755383, compound

Product 1

HCID 19755396HCID 19755396, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

To 454 mg (1 mmol) of ester from Step 5 in THF (15 ml) at -78° C. is added lithium hexamethyldisilazide in toluene (1.1 mmol), followed by hexamethylphosphoramide (1.5 ml). After 15 minutes, p-chlorobenzyl bromide (300 mg) is added and the reaction is allowed to warm to room temperature. The reaction mixture is then poured into 5% aqueous NH4Cl, extracted with 2×100 ml Et2O and the organic extracts dried over MgSO4. Filtration and evaporation of the solvent left a crude residue, which, after chromatography over silica using EtOAc-hexane, yields ethyl 9-p-chlorobenzyl-6-(quinolin-2-ylmethoxy)-5-allyl-1,2,3,4-tetrahydrocarbazol-1-ylacetate.

Workup

  1. extractionextracted with 2×100 ml Et2O
  2. dry with materialthe organic extracts dried over MgSO4
  3. filtrationFiltration and evaporation of the solvent
  4. waitleft a crude residue, which

Sources & evidence

ORD record
ord-2b4896261f494d11bbdb6d9719731c15
Source dataset
uspto-grants-1993_06
Patent number
US05221678

Reaction notes

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