Reaction #70099

Reaction equation

pyridine

Triphosgene

bis(trichloromethyl)carbonate

1,3-O-benzylideneglycerol

→

2-phenyl-1,3-dioxan-5-yl carbonochloridate

Solvents

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONUpon completion of the addition the reaction mixture
2. 2
   workup.STIRRINGwas stirred for 30 min at −40° C
3. 3
   Temperatureto warm to 0° C. over 60 min
4. 4
   Temperaturesubsequently warmed to rt over 3.5 h
5. 5
   workup.STIRRINGunder stirring
6. 6
   OtherThe reaction product was used in the next step without any further purification

Procedure

Triphosgene (bis(trichloromethyl)carbonate (13.35 g, 45.0 mmol) was added under argon at room temperature to a solution of 1,3-O-benzylideneglycerol (18.02 g, 100.0 mmol) in dry CH2Cl2 (300 ml). The reaction mixture was cooled to −40° C. and a solution of pyridine (10.9 ml, 135.0 mmol) was added over 35 min under stirring. Upon completion of the addition the reaction mixture was stirred for 30 min at −40° C. Then it was allowed to warm to 0° C. over 60 min and subsequently warmed to rt over 3.5 h under stirring. The reaction product was used in the next step without any further purification

Source