(3-hydroxyphenyl)boronic Acid → 3-(2,8-Dimethoxy-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenol

HRID 2218696

Reaktionsgleichung

Reaktionsgleichung von HRID 2218696
[OH:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[CH:12]=[C:13]1[C:19]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:18]=2[CH2:17][CH2:16][C:15]2[CH:26]=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:14]1=2>>[CH3:25][O:24][C:22]1[CH:21]=[CH:20][C:19]2[C:13](=[CH:12][C:6]3[CH:7]=[C:2]([OH:1])[CH:3]=[CH:4][CH:5]=3)[C:14]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][C:15]=3[CH2:16][CH2:17][C:18]=2[CH:23]=1

Komponenten

3

Edukt 2

HCID 2734359(3-hydroxyphenyl)boronic AcidHCID 689363135-bromomethylene-2,8-dimethoxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Produkt 1

HCID 597704413-(2,8-Dimethoxy-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenolAusbeute 33,5 %

Versuchsvorschrift

Following procedures essentially as described in Example 219, below, and using 3-hydroxyphenyl boronic acid (304 mg, 2.2 mmol) with 5-bromomethylene-2,8-dimethoxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (690 mg, 2 mmol) to give 990 mg crude product. Purify the crude product using column chromatography eluting with 8% EtOAc/hexane to 25% EtOAc/hexane to give 240 mg (33%) product as a colorless oil. MS (ES) 357 (M−1). HPLC shows 99% purity at t=3.33 min.

Aufarbeitung

  1. customto give 990 mg crude product
  2. customPurify the crude product
  3. washeluting with 8% EtOAc/hexane to 25% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b453d8e45af74b3580af129c93dfe9b5
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07411072B2

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