Reaktion #668793

Reaktionsgleichung

acetylide

tert-butyl-[(1S,4aR,5R,8aR)-5-((R)-4,4-dibromo-1-methyl-but-3-enyl)-4a-methyl-decahydro-naphthalen-1-yloxy]-dimethyl-silane

nBuLi

acetone

→

title compound

Ausbeute 79.1%

(R)-6-[(1R,4aR,5S,8aR)-5-(tert-Butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-2-methyl-hept-3-yn-2-ol

Ausbeute 79.1%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe temperature maintained for 1 h
2. 2
   Sonstigeto react for 30 minutes
3. 3
   SonstigeThe reaction was quenched
4. 4
   workup.ADDITIONby pouring
5. 5
   Sonstigeonto crushed ice/NH4Cl
6. 6
   Extraktionextracted twice with ether
7. 7
   Waschenwashed with water and brine
8. 8
   Trocknendried over sodium sulfate
9. 9
   Sonstigeevaporated to dryness

Vorschrift

3.05 g (6.00 mmol) of tert-butyl-[(1S,4aR,5R,8aR)-5-((R)-4,4-dibromo-1-methyl-but-3-enyl)-4a-methyl-decahydro-naphthalen-1-yloxy]-dimethyl-silane was dissolved in 35 ml of abs. THF and cooled down to -78°. 11.6 ml of nBuLi (1.55M, hexane) was slowly added and the temperature maintained for 1 h. 2.15 ml (29.3 mmol) of acetone, dissolved in 5 ml of abs. THF, was then added to the resultant acetylide-solution and allowed to react for 30 minutes. The reaction was quenched by pouring onto crushed ice/NH4Cl, extracted twice with ether, washed with water and brine, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=9/1) yielded 1.93 g of the title compound as colorless oil.

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