Reaction #57416

Reaction equation

methanol

1-bromoadamantane

(2,2-dichloro-1-methoxy-vinyloxy)-trimethylsilane

dichloromethane

→

adamantan-1-yl-dichloro-acetic acid methyl ester

Solvents

heptane

water

Conditions

Workup

1. 1
   OtherA 1 liter flask equipped with an argon inlet
2. 2
   OtherThe organic layer was separated
3. 3
   Washwashed with water (2×100 ml), 1 N sodium bicarbonate (3×150 ml), and water (2×200 ml)
4. 4
   FiltrationThe resulting solution was filtered though a pad of Celite 545 and filtrate
5. 5
   Concentrationwas concentrated at reduced pressure
6. 6
   Otherto give a colorless solid
7. 7
   workup.DISSOLUTIONThis material was dissolved
8. 8
   Temperatureto cool to room temperature for 1 hour
9. 9
   TemperatureAfter cooling to approximately 5° C. for 2 hours
10. 10
    Filtrationthe solid was collected by filtration
11. 11
    Washwashed with cold methanol:water (94:6; 4×50 ml)

Procedure

A 1 liter flask equipped with an argon inlet was charged with crude (2,2-dichloro-1-methoxy-vinyloxy)-trimethylsilane (129.1 g, approximately 0.389 mol) and anhydrous dichloromethane (100 ml). To the resulting solution was added 1-bromoadamantane (75.2 g, 0.349 mol) and anhydrous zinc chloride (6.56 g, 48 mmol). The resulting mixture was allowed to stir at room temperature overnight. The resulting red-brown mixture was diluted with heptane (600 ml) and water (300 ml). The organic layer was separated and washed with water (2×100 ml), 1 N sodium bicarbonate (3×150 ml), and water (2×200 ml). The resulting solution was filtered though a pad of Celite 545 and filtrate was concentrated at reduced pressure to give a colorless solid. This material was dissolved in boiling methanol (250 ml). The resulting solution was allowed to cool to room temperature for 1 hour. After cooling to approximately 5° C. for 2 hours, the solid was collected by filtration and washed with cold methanol:water (94:6; 4×50 ml) to give adamantan-1-yl-dichloro-acetic acid methyl ester (Formula VII) as a colorless solid: 75.0 grams (77.3% based on 1-bromoadamantane); mp 76.3° C.

Source