1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → tert-Butyl (3-chloro-6-hydroxy-1H-indol-1-yl)acetate

HRID 1767919Notes

Reaction equation

HRID 1767919 reaction equation
[C:1]([O:5][C:6](=[O:26])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][Si](C(C)(C)C)(C)C)[CH:15]=2)[C:10]([Cl:25])=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:1]([O:5][C:6](=[O:26])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[C:10]([Cl:25])=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 69283059[6-(Tert-butyl-dimethyl-silanyloxy)-3-chloro-indol-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 69283057tert-Butyl (3-chloro-6-hydroxy-1H-indol-1-yl)acetate

Procedure

In analogy to the procedure described in example 3 b], [6-(tert-butyl-dimethyl-silanyloxy)-3-chloro-indol-1-yl]-acetic acid tert-butyl ester was treated with tetrabutylammonium fluoride hydrate to obtain (3-chloro-6-hydroxy-indol-1-yl)-acetic acid tert-butyl ester as colorless gum.

Sources & evidence

ORD record
ord-7c9cad1ffbf04caa8ce3c8c6df4c3961
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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