Reaktion #791993

Reaktionsgleichung

(-)-(E)-1-3(-Phenoxyphenyl)but-1-en-3-ol

(-)-(E)-1-(3-phenoxyphenyl)but-1-en-3-ol

N,O-bis(t-butoxycarbonyl)hydroxylamine

DEAD

triphenylphosphine

→

desired product

N,O-bis(t-butoxycarbonyl)-N-[1-methyl-3-(3-phenoxyphenyl)prop -2-en-1-yl]hydroxylamine

Lösungsmittel

ether

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room tempterature
2. 2
   Sonstigeto precipitate Ph3P=O as a dark gummy mass
3. 3
   SonstigeThe mother liquor was decanted off
4. 4
   Sonstigeto give a tan/orange oil which
5. 5
   Waschenwas eluted through a silica gel column
6. 6
   Sonstigeto give a pale yellow oil which
7. 7
   Waschenwas eluted through a second silica gel column

Vorschrift

(-)-(E)-1-3(-Phenoxyphenyl)but-1-en-3-ol from step (d) (2.6 g), N,O-bis(t-butoxycarbonyl)hydroxylamine (2.65 g), and triphenylphosphine (4.25 g) were taken up in toluene (30 ml) and cooled to -78° C. under N2. A solution of DEAD (2.9 g) in toluene (10 ml) was then added and the mixture allowed to warm to room tempterature. 40/60 pet.ether (60 ml) was added to precipitate Ph3P=O as a dark gummy mass. The mother liquor was decanted off and stripped to give a tan/orange oil which was eluted through a silica gel column using methylene chloride. The eluate was stripped to give a pale yellow oil which was eluted through a second silica gel column using ether/methylene chloride/40-60 pet.ether (1:1:8) and the eluate stripped to give the desired product as a colourless oil which was dried under high vacuum. Yield 1 97 g.

Quelle