Monobenzone → 1-(diphenylmethyl)-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-4,6-dimethoxy-1,3-dihydro-2H-indol-2-one

HRID 2385136Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1C=CC=CC=1.BrC1C=C([OH:23])C=CC=1.[C:24]1([CH:30]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[N:31]2[C:39]3[C:34](=[C:35]([O:42][CH3:43])[CH:36]=[C:37]([O:40][CH3:41])[CH:38]=3)[C:33](=[O:44])[C:32]2=[O:45])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.FC(F)(F)C1OC(CN2C3C(=CC=CC=3)C(=O)C2=O)=CC=1>>[C:46]1([CH:30]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:31]2[C:39]3[C:34](=[C:35]([O:42][CH3:43])[CH:36]=[C:37]([O:40][CH3:41])[CH:38]=3)[C:33]([OH:44])([C:13]3[C:12]([OH:15])=[CH:11][C:10]4[O:23][CH2:2][CH2:1][O:8][C:9]=4[CH:14]=3)[C:32]2=[O:45])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

Reactant 4

HCID 7638Monobenzone

HCID 115633-Bromophenol

HCID 673564881-((5-(Trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dione

HCID 673570521-(diphenylmethyl)-4,6-dimethoxy-1H-indole-2,3-dione

Product 1

HCID 673564501-(diphenylmethyl)-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-4,6-dimethoxy-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2A and making non-critical variations using 4-(benzyloxy)phenol to replace 3-bromophenol, and 1-(diphenylmethyl)-4,6-dimethoxy-1H-indole-2,3-dione to replace 1-((5-(trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dione, 1-(diphenylmethyl)-3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-4,6-dimethoxy-1,3-dihydro-2H-indol-2-one was obtained (50%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.81 (s, 1H), 7.34-7.16 (m, 10H), 6.82 (s, 1H), 6.55 (s, 1H), 6.31 (s, 1H), 6.14 (d, J=1.8 Hz, 1H), 5.64 (d, J=1.8 Hz, 1H), 4.22-4.10 (m, 4H), 3.92 (s, 1H), 3.77 (s, 3H), 3.49 (s, 3H).

Sources & evidence

ORD record: ord-fa0a6066f37949ae85608ef9480858b1
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263606B2

Reaction notes

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