Pyridine → HCID 23362790, compound

HRID 1081567Notes

Reaction equation

HRID 1081567 reaction equation
Cl[C:2]([O:4][CH:5]([Cl:7])[CH3:6])=[O:3].[CH2:8]([CH:10]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]1)[CH3:9].N1C=CC=CC=1>ClCCl>[C:2](=[O:3])([O:16][CH:13]1[CH2:14][CH2:15][CH:10]([CH2:8][CH3:9])[CH2:11][CH2:12]1)[O:4][CH:5]([Cl:7])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 782934-EthylcyclohexanolHCID 5213051-Chloroethyl chloroformate

Product 1

HCID 23362790HCID 23362790, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 1-chloroethyl chloroformate (5.46 g) in dry dichloromethane (20 ml) was added dropwise, under nitrogen at 0°, to a stirred solution of 4-ethylcyclohexanol (5 g) in dry dichloromethane (20 ml) in presence of 3A molecular sieves. A solution of pyridine (3 g) in dry dichloromethane (20 ml) was added dropwise to the reaction mixture during 20 min at 0° the mixture was then warmed to 20°, stirred for 20 hours, washed with brine (2×50 ml) and dried. The solvent was removed under vacuum and the residue was distilled to give the title compound as a colourless oil (7.9 g; b.p. 130°/5.2 mbar; t.l.c. cyclohexane/ethyl acetate 9/1 Rf=0.88; IR (CDCl3), Vmax (cm-1): 1757 (C=O); 1H-NMR (300 MHz, CDCl3): 6.43 (q), 6.42 (q), 4.93 (bs), 4.59 (tt), 2.14-2.01 (bs), 2.00-1.88 (bs), 1.88-1.78 (m), 1.83 (d), 1.82 (d), 1.60-1.50 (m), 1.50-1.32 (m), 1.30-1.15 (m), 1.28-1.18 (m) 1.05-0.95 (m), 0.95-0.85 (m).

Workup

  1. temperaturewas then warmed to 20°
  2. washwashed with brine (2×50 ml)
  3. customdried
  4. customThe solvent was removed under vacuum
  5. distillationthe residue was distilled

Sources & evidence

ORD record
ord-511d3a77418a4588b1628c0214152138
Source dataset
uspto-grants-1996_12
Patent number
US05587374

Reaction notes

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