Pyridine → 2-Phenyl-1,3-dioxan-5-yl carbonochloridate

HRID 1479224Notes

Reaction equation

HRID 1479224 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH2:13]1[O:18][CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:16][CH2:15][CH:14]1[OH:25].N1C=CC=CC=1>C(Cl)Cl>[C:2]([Cl:1])(=[O:4])[O:25][CH:14]1[CH2:13][O:18][CH:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:16][CH2:15]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 743621,3-Dioxan-5-ol, 2-phenyl-HCID 94429Triphosgene2×

Product 1

HCID 584552732-Phenyl-1,3-dioxan-5-yl carbonochloridate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

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

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. stirringwas stirred for 30 min at −40° C
  3. temperatureto warm to 0° C. over 60 min
  4. temperaturesubsequently warmed to rt over 3.5 h
  5. stirringunder stirring
  6. customThe reaction product was used in the next step without any further purification

Sources & evidence

ORD record
ord-d1dbaa34f2f6443b8cc2d0d19bafe099
Source dataset
uspto-grants-2016_08
Patent number
US09408919B2

Reaction notes

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