1'-benzhydryl-6-(benzyloxy)-2H-spiro[benzofuran-3,3'-indolin]-2'-one → 1'-(diphenylmethyl)-5-hydroxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 1407611Notes

Reaction equation

HRID 1407611 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:39][CH2:38][C:15]3([C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]([CH:24]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:16]3=[O:37])[C:13]=2[CH:14]=1)C1C=CC=CC=1.C(OC1C=CC2C3(COC=2C=1)C1C(=CC=CC=1)N(C(C1C=CC=CC=1)C1C=CC=CC=1)C3=O)C1C=CC=CC=1>>[C:31]1([CH:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]3([C:13]4[CH:14]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=4[O:39][CH2:38]3)[C:16]2=[O:37])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 461941811'-benzhydryl-6-(benzyloxy)-2H-spiro[benzofuran-3,3'-indolin]-2'-oneHCID 593527575-(benzyloxy)-1'-(diphenylmethyl)spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Product 1

HCID 592634041'-(diphenylmethyl)-5-hydroxyspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

Procedure

Following the procedure as described in EXAMPLE 2.68 and making non-critical variations using 5-(benzyloxy)-1′-(diphenylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one to replace 6-(benzyloxy)-1′-(diphenylmethyl)spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one, 1′-(diphenylmethyl)-5-hydroxyspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one was obtained (78%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.22 (br s, 1H), 7.30-7.08 (m, 10H), 7.02-6.93 (m, 1H), 6.88 (s, 1H), 6.85-6.75 (m, 2H), 6.65-6.49 (m, 2H), 6.38-6.26 (m, 1H), 6.13-6.02 (m, 1H), 4.65 (ABq, 2H).

Sources & evidence

ORD record
ord-e3b2081a84cc45759916dda4ecef79b9
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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