Sesamol → 1-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-2,3-dihydro-1-benzofuran-6-yl)-1,3-dihydro-2H-indol-2-one

HRID 425515Notes

Reaction equation

HRID 425515 reaction equation
O1C2C=CC(O)=CC=2OC1.[O:11]1[C:15]2[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:14]=2[CH2:13][CH2:12]1.C1(CCN2C3C(=CC=CC=3)C(=O)C2=O)CC1.[C:37]1([CH:43]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[N:44]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46](=[O:53])[C:45]2=[O:54])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[C:55]1([CH:43]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:44]2[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:46]([OH:53])([C:17]3[C:18]([OH:20])=[CH:19][C:14]4[CH2:13][CH2:12][O:11][C:15]=4[CH:16]=3)[C:45]2=[O:54])[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1

Participants

5

Reactant 4

HCID 68289SesamolHCID 19692771-(diphenylmethyl)-1H-indole-2,3-dioneHCID 111263112,3-Dihydro-5-hydroxybenzo(b)furanHCID 655965701-(2-cyclopropylethyl)-1H-indole-2,3-dione

Product 1

HCID 120042501-(diphenylmethyl)-3-hydroxy-3-(5-hydroxy-2,3-dihydro-1-benzofuran-6-yl)-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2B, and making non-critical variations to replace 1,3-benzodioxol-5-ol with 2,3-dihydrobenzofuran-5-ol, (Alabaster, R. J., et al.; Synthesis (1988), 12:950-2) and 1-(2-cyclopropylethyl)-1H-indole-2,3-dione with 1-(diphenylmethyl)-1H-indole-2,3-dione, the title compound was obtained: MS (ES+) m/z 472.2 (M+23).

Sources & evidence

ORD record
ord-1edc83fe48db4c7a8aeae15ed7f93fc3
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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