3-Hydroxyacetyl-5-(benzyloxy)indole → 3-Glyoxalyl-5-(benzyloxy)indole

HRID 1607611Notes

Reaction equation

HRID 1607611 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)[NH:7][CH:6]=1)=[O:4]>C(O)C.C(O)(=O)C.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:3]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=2)[NH:7][CH:6]=1)(=[O:4])[CH:2]=[O:1]

Participants

5

Reactant 1

HCID 141683033-Hydroxyacetyl-5-(benzyloxy)indole

Product 1

HCID 141683043-Glyoxalyl-5-(benzyloxy)indole

Reagents, catalysts & solvents 3

HCID 165397Cupric acetate monohydrateCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A solution of 20 in ethanol was treated with copper(II) acetate monohydrate in 50% aqueous acetic acid as described above for 15. Work-up gave nearly pure 3-glyoxalyl-5-(benzyloxy)indole 21.

Sources & evidence

ORD record
ord-d0acd63e38724b65b9cfcf0f86105429
Source dataset
uspto-grants-1989_09
Patent number
US04866084

Reaction notes

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