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

HRID 545792Notes

Reaction equation

HRID 545792 reaction equation
O1C2C=CC(O)=CC=2OC1.[O:11]1[C:15]2[CH:16]=[C:17]([OH:20])[CH:18]=[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:18]3[C:17]([OH:20])=[CH:16][C:15]4[O:11][CH2:12][CH2:13][C:14]=4[CH:19]=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 122365402,3-Dihydro-1-benzofuran-6-olHCID 655965701-(2-cyclopropylethyl)-1H-indole-2,3-dione

Product 1

HCID 588725551-(diphenylmethyl)-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-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-6-ol (Foster et al., J. Chem. Soc. 1948:2254-2258) and 1-(2-cyclopropylethyl)-1H-indole-2,3-dione with 1-(diphenylmethyl)-1H-indole-2,3-dione, the title compound was obtained (68%) as a white solid: MS (ES+) m/z 450.4 (M+1).

Sources & evidence

ORD record
ord-3fd8412d536d4b2fb12c2bf0cac39186
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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