Reaction #2195475

Reaction equation

4,4′-dimethoxytrityl chloride

3-Dimethylamino-1,2-propanediol

4,4′-Dimethoxytrityl chloride

4,4′-dimethoxytrityl chloride

→

yellow gum

Yield 105.3%

1-(4,4′-Dimethoxytrityloxy)-3-dimethylamino-2-propanol

Yield 105.3%

Solvents

pyridine

pyridine

Conditions

Workup

1. 1
   OtherThe flask was sealed
2. 2
   Otherflushed with argon
3. 3
   workup.ADDITIONcharged with pyridine
4. 4
   Othersealed
5. 5
   Otherto come to room temperature
6. 6
   ConcentrationThe reaction was concentrated in vacuo
7. 7
   workup.DISSOLUTIONre-dissolved in dichloromethane (300 mL)
8. 8
   WashThe organic phase was washed with saturated bicarbonate (2×200 mL) and brine (1×200 mL)
9. 9
   Dryingdried over MgSO4
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated
12. 12
    Otherdried under high vacuum

Procedure

3-Dimethylamino-1,2-propanediol (6.0 g, 50 mmol) was weighed into a 1 L round bottomed flask with a stir bar. The flask was sealed, flushed with argon, charged with pyridine and cooled to 0° C. 4,4′-Dimethoxytrityl chloride (17.9 g, 1.05 equiv.) was weighed into a 100 mL round bottomed flask, sealed and then dissolved in pyridine (80 mL). The 4,4′-dimethoxytrityl chloride solution was transferred to the stirring reaction mixture slowly, using additional fresh pyridine (20 mL) to effect the transfer of residual 4,4′-dimethoxytrityl chloride. The reaction was allowed to come to room temperature while stirring overnight. The reaction was concentrated in vacuo and re-dissolved in dichloromethane (300 mL). The organic phase was washed with saturated bicarbonate (2×200 mL) and brine (1×200 mL), dried over MgSO4, filtered, concentrated and dried under high vacuum to afford 22.19 g of a yellow gum that was used without further purification.

Source