Sodium Iodide → 3-[3'-Adamantan-1-yl-4'-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethoxy)-biphenyl-4-yl]acrylic acid tert-butyl ester

HRID 41722

Reaktionsgleichung

Reaktionsgleichung von HRID 41722
[C:1]([O:5][C:6](=[O:32])/[CH:7]=[CH:8]/[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:22]34[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]5)[CH2:23]3)[CH2:29]4)[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:34][N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>>[C:1]([O:5][C:6](=[O:32])[CH:7]=[CH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:34][N:35]3[C:39](=[O:40])[C:38]4[C:37](=[CH:44][CH:43]=[CH:42][CH:41]=4)[C:36]3=[O:45])=[C:17]([C:22]34[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]5)[CH2:23]3)[CH2:29]4)[CH:16]=2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 87154ChloromethylphthalimideHCID 86660473HCID 86660473, Verbindung

Produkt 1

HCID 674428563-[3'-Adamantan-1-yl-4'-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethoxy)-biphenyl-4-yl]acrylic acid tert-butyl esterAusbeute 55 %

Versuchsvorschrift

A solution of (E)-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)acrylic acid tert-butyl ester (200 mg, 0.464 mmol), N-chloromethylphthalimide (91 mg, 0.464 mmol), K2CO3 (70 mg, 0.464 mmol) and NaI (70 mg, 0.464 mmol) was stirred overnight at RT in the dark. The solvent was evaporated and the residue was taken up in EtOAc. The organic phase was washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure. 3-[3′-Adamantan-1-yl-4′-(1,3-dioxo-1,3-dihydroisoindol-2-ylmethoxy)-biphenyl-4-yl]acrylic acid tert-butyl ester was obtained after purification on silica gel (EtOAc/hexane 15:85) in 55% yield (150 mg).

Aufarbeitung

  1. customThe solvent was evaporated
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-512abd97103a4b919238c34384965674
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530517B2

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