Pyridine → HCID 55303130, compound

HRID 1169969Notes

Reaction equation

HRID 1169969 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.N1C=CC=CC=1.[C:12](Cl)(=[O:16])[O:13][CH2:14][Cl:15].C(OCC)C>ClCCl>[C:12](=[O:16])([O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)[O:13][CH2:14][Cl:15]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 62754Chloromethyl chloroformateHCID 75644Cyclopropanemethanol

Product 1

HCID 55303130HCID 55303130, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of cyclopropylmethanol (0.39 ml, 5.0 mmol) and pyridine (0.40 ml, 5.0 mmol) in dichloromethane (4 ml), at 0° C. and under nitrogen, was added dropwise chloromethyl chlorocarbonate (0.40 ml, 4.5 mmol). The reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 2 h. To the mixture was added diethyl ether (15 ml) and the solid material was collected by filtration and washed with diethyl ether (10 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo to give the title compound (725 mg) which was used directly.

Workup

  1. waitat room temperature for 2 h
  2. filtrationthe solid material was collected by filtration
  3. washwashed with diethyl ether (10 ml)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e53b6b5698554f1a98b74639aa6a7911
Source dataset
uspto-grants-2010_11
Patent number
US07825149B2

Reaction notes

Loading…