Reaction #1244275

Reaction equation

water

EtOAc

EtOAc

triethylorthoacetate

2-Azidopropane-1,3-diol

→

24

Yield 57.3%

2-Azido-3-hydroxypropyl acetate

Yield 57.3%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Concentrationconcentrated in vacuo
2. 2
   OtherPurification of the residue on a silica gel cartridge

Procedure

2-Azidopropane-1,3-diol 23 (10.46 g, 89.3 mmol) was dissolved in CH2Cl2 (450 mL) and treated with a catalytic amount of p-toluene sulfonic acid monohydrate (340 mg, 1.8 mmol) and triethylorthoacetate (24.4 mL, 134 mmol) at room temperature for 1 hr. After the formation of the orthoester was complete, a stoichiometric amount of water (2.4 mL, 134 mmol) was added to the mixture. The mixture was then stirred for 40 min and then concentrated in vacuo. Purification of the residue on a silica gel cartridge using EtOAc:Hex as the eluent (5% EtOAc to 100% EtOAc) afforded 8.14 g (57% yield) of 24 as a clear, colorless oil. 1H NMR (CDCl3, 400 MHz), δ: 2.45 (1H, br s), 2.12 (3H, s), 3.63-3.78 (3H, m), 4.20-4.30 (2H, m).

Source