Triethylamine → 1,3-Bis(benzyloxy)propan-2-one

A mixture of sulfur trioxide/pyridine complex (2.33 g, 4 equivalents) in DMSO (3 ml) and triethylamine (2.05 ml, 4 equivalents) was stirred to give a pale yellow solution. To this was added a solution of 1,3-dibenzyloxy-2-propanol (1 g) in DMSO (1 ml) over 2 minutes. (The reaction mixture was kept in a water bath). The temperature of the reaction mixture reached 30° C. After 10 minutes the water bath was removed and the reaction mixture was stirred at room temperature (ca 20-25° C.) for 3 hours. The reaction mixture was diluted with ethyl acetate (15 ml) and water (15 ml), stirred and the organic extract was separated. The organic extract was washed with 5% w/v sodium chloride (2×10 ml) and water (10 ml). The separated organic extract was concentrated in vacuo to give an oil which solidified to provide 0.75 g of 1,3-dibenzyloxy-2-propanone in 75.8% yield. An NMR spectrum of product was concordant with a reference sample.

1. customto give a pale yellow solution
2. custom(The reaction mixture was kept in a water bath
3. customreached 30° C
4. customAfter 10 minutes the water bath was removed
5. stirringthe reaction mixture was stirred at room temperature (ca 20-25° C.) for 3 hours
6. additionThe reaction mixture was diluted with ethyl acetate (15 ml) and water (15 ml)
7. stirringstirred
8. extractionthe organic extract
9. customwas separated
10. extractionThe organic extract
11. washwas washed with 5% w/v sodium chloride (2×10 ml) and water (10 ml)
12. extractionThe separated organic extract
13. concentrationwas concentrated in vacuo
14. customto give an oil which

ORD record

ord-cfcde5be1c8a462fabf4e1ec897298b5

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947727B2