Reaktion #475929

Reaktionsgleichung

indium

Indium

compound

tert-butyl({(1R,5S)-2-(iodomethyl)-5-[(triethylsilyl)oxy]cyclohex-2-en-1-yl}oxy)dimethylsilane

formaldehyde

→

titled compound

Ausbeute 68.5%

(1S,3R,5R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-(hydroxymethyl)-4-methylenecyclohexanol

Ausbeute 68.5%

Lösungsmittel

tetrahydrofuran

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction toward completion
2. 2
   Extraktionextracted twice with 250 mL each of ethyl acetate
3. 3
   WaschenThe combined organic layers were washed sequentially with 5% NaHCO3 and brine
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigePurification by silica gel chromatography (
8. 8
   Waschen200 mL of SiO2, elution with a gradient of 1:1 to 3:1 ethyl acetate

Vorschrift

The compound of Example 16G (2.5 g, 5.2 mmol) was dissolved in 20 mL of water and 30 mL of tetrahydrofuran. Indium powder (0.90 g) was added followed by formaldehyde (37% aqueous solution, 1.6 mL, 21 mmol). Two additional portions of indium (0.3 g each) were added to drive the reaction toward completion. The reaction was diluted with 180 mL of water and extracted twice with 250 mL each of ethyl acetate. The combined organic layers were washed sequentially with 5% NaHCO3 and brine, then dried over MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (200 mL of SiO2, elution with a gradient of 1:1 to 3:1 ethyl acetate:hexanes) afforded the titled compound (0.97 g, 68%).

Quelle