Chloromethyl benzoate → Benzoyloxymethyl 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylate

HRID 1605102Notes

Reaction equation

HRID 1605102 reaction equation
[C:1]([N:9]1[C:21]2[CH2:20][CH2:19][CH:18]([C:22]([OH:24])=[O:23])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[K+].[C:30]([O:38][CH2:39]Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C=O>[C:1]([N:9]1[C:21]2[CH2:20][CH2:19][CH:18]([C:22]([O:24][CH2:39][O:38][C:30](=[O:37])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:23])[CH2:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79257Chloromethyl benzoateHCID 516893Potassium BicarbonateHCID 53880483HCID 53880483, compound

Product 1

HCID 21548557Benzoyloxymethyl 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure similar to that of Example 45 but using 12.8 g. of 9-benzoyl-1,2,3,4-tetrahydrocarbazole-3-carboxylic acid, 20 g. of potassium bicarbonate, 10 ml. of chloromethyl benzoate in 50 ml. of dry dimethylformamide there was obtained, after filtration of the ether extract through silica gel followed by combination of those fractions showing only one identical spot on thin layer chromotography and evaporation to dryness under reduced pressure, 14 g. of the title compound; m.p. 84°-86°C. (methyl alcohol).

Workup

  1. filtrationafter filtration of the ether
  2. extractionextract through silica gel
  3. customon thin layer chromotography and evaporation to dryness under reduced pressure, 14 g

Sources & evidence

ORD record
ord-13fd246db595488f9ab517077addc1a1
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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