Formaldehyde → 4-Benzyloxy-1-hydroxymethylindole

HRID 490812Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]=[O:19].[OH-].[Na+]>>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH2:18][OH:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 712Formaldehyde

HCID 14798Sodium Hydroxide

HCID 884654-(phenylmethoxy)-1H-indole

Product 1

HCID 247769004-Benzyloxy-1-hydroxymethylindole

Procedure

Compounds of Formula I also can be prepared as illustrated by exemplary reaction in Scheme 2. Reaction of 4-benzyloxy-indole with formaldehyde in the presence of a base such as NaOH produced 4-benzyloxy-1-hydroxymethyl-indole. The benzyl protecting group was removed by hydrogenation to give the 4-hydroxy-1-hydroxymethyl-indole. Reaction of 4-hydroxy-1-hydroxymethyl-indole with an aryl-aldehyde, such as 5-bromoveratraldehyde and malononitrile in the presence of a base, such as piperidine produced the substituted 7-hydroxymethyl-pyrrolo[2,3-h]chromene.

Workup

customCompounds of Formula I also can be prepared
customas illustrated by exemplary reaction in Scheme 2

Sources & evidence

ORD record: ord-e083e2d71a5042289a64b63e333441c2
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528164B2

Reaction notes

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