Pyridine → HCID 55303130, compound

HRID 1985901Notes

Reaction equation

HRID 1985901 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 drop wise 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-9d45503f026e4a00a4c9e3deba1e47f4
Source dataset
uspto-grants-2009_06
Patent number
US07547718B2

Reaction notes

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