1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → 6-Hydroxyskatole

HRID 1767985Notes

Reaction equation

HRID 1767985 reaction equation
C([Si](C)(C)[N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][Si](C(C)(C)C)(C)C)[CH:13]=2)[C:8]([CH3:23])=[CH:7]1)(C)(C)C.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH3:23][C:8]1[C:9]2[C:14](=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[NH:6][CH:7]=1

Participants

3

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 236144811-(tert-butyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1H-indole

Product 1

HCID 136625956-Hydroxyskatole

Procedure

In analogy to the procedure described in example 27 d], 1-(tert-butyl-dimethyl-silanyl)-6-(tert-butyl-dimethyl-silanyloxy)-3-methyl-1H-indole was treated with tetrabutylammonium fluoride hydrate to obtain 3-methyl-1H-indol-6-ol as brown crystals.

Workup

  1. customdescribed in example 27 d

Sources & evidence

ORD record
ord-ff0e8d993e954042b29c36ac39d63405
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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