Tetrabutylammonium Fluoride → Methyl E4-[5-[2-(4-tert-butylbenzyloxy)phenyl]-3-(3,5-difluoro-4-hydroxybenzyl)pent-4-enyl]-benzoate

HRID 1921889Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921889
[C:1]([C:5]1[CH:53]=[CH:52][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:32][C:33]2[CH:38]=[C:37]([F:39])[C:36]([O:40][Si](C(C)C)(C(C)C)C(C)C)=[C:35]([F:51])[CH:34]=2)[CH2:20][CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:32][C:33]2[CH:38]=[C:37]([F:39])[C:36]([OH:40])=[C:35]([F:51])[CH:34]=2)[CH2:20][CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)=[CH:52][CH:53]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 57971919HCID 57971919, Verbindung

Produkt 1

HCID 57971935Methyl E4-[5-[2-(4-tert-butylbenzyloxy)phenyl]-3-(3,5-difluoro-4-hydroxybenzyl)pent-4-enyl]-benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

780 mg (1.05 mmol) of methyl E-4-[5-[2-(4-tert-butylbenzyloxy)phenyl]-3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)pent-4-enyl]benzoate are introduced into 20 ml of THF at room temperature under argon, 2.11 ml (2.11 mmol) of a 1 M solution of tetra-n-butylammonium fluoride in THF are added, and the mixture is stirred at room temperature until reaction is complete. All the volatile components are then removed in vacuo. The resulting crude product is purified by preparative HPLC. 229 mg (37% of theory) of the title compound are obtained.

Aufarbeitung

  1. customAll the volatile components are then removed in vacuo
  2. customThe resulting crude product is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c67f009f71944fc298f713e35bb4652a
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173704B2

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