Reaktion #745154

ord-dc1d712eccde433584748b29deeaf624

Reaktionsgleichung

CCOC(C)=O
EA
COc1c(O)cc(C(C)=O)cc1C(C)(C)C
1-(3-tert-Butyl-5-hydroxy-4-methoxyphenyl)ethanone
BrCCCOC1CCCCO1
2-(3-bromo-propoxy)tetrahydropyran
[H-].[Na+]
sodium hydride
→
COc1c(OCCCOC2CCCCO2)cc(C(C)=O)cc1C(C)(C)C
title compound
Ausbeute 112.3%
COc1c(OCCCOC2CCCCO2)cc(C(C)=O)cc1C(C)(C)C
1-{3-tert-Butyl-4-methoxy-5-[3-(tetrahydropyran-2-yloxy)propoxy]phenyl}ethanone
Ausbeute 112.3%

Edukte

CCOC(C)=O
EA
COc1c(O)cc(C(C)=O)cc1C(C)(C)C
1-(3-tert-Butyl-5-hydroxy-4-methoxyphenyl)ethanone
BrCCCOC1CCCCO1
2-(3-bromo-propoxy)tetrahydropyran
[H-].[Na+]
sodium hydride

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    WaschenThe EA phase was washed with water
  2. 2
    Sonstigedried
  3. 3
    Einengenconcentrated

Vorschrift

1-(3-tert-Butyl-5-hydroxy-4-methoxyphenyl)ethanone (O3.070; 6.9 g) and 2-(3-bromo-propoxy)tetrahydropyran (8.31 g) were dissolved in DMF (80 ml), and sodium hydride (894 mg) was added. After stirring at RT for 5 hours, the solvent was drawn off and the residue was taken up with EA. The EA phase was washed with water, dried and concentrated. 12.7 g of the title compound were obtained as a crude product in sufficient purity.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08076336B2uspto-grants-2011_12