Pyridinium chloride → HCID 3243908, compound

HRID 326297Notes

Reaction equation

HRID 326297 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:16][C:10]3([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[CH2:9][C:8](=[O:17])[C:7]=2[CH:18]=1.Cl.N1C=CC=CC=1>>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[O:16][C:10]3([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[CH2:9][C:8](=[O:17])[C:7]=2[CH:18]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 19736723HCID 19736723, compound

Product 1

HCID 3243908HCID 3243908, compoundYield 85.9%

Procedure

A mixture of 6-methoxyspiro[2H-1-benzopyran-2,1'-cyclohexan]-4(3H)-one (prepared in Preparation 3) (1.0 g, 4.06 mmol) in dry pyridine HCl (6 g, 52 mmol) is heated to 210°-215° C. on an oil bath for 45 minutes with stirring, and allowed to cool. The mixture is extracted with water and diethyl ether. The ether layer is separated, washed with dilute hydrochrolic acid and then water, dried and concentrated. The residue is placed on a silica gel column and eluted with a mixture of acetonitrile and dichloromethane (1:9 to 1:4) to obtain the title compound as an oil (0.81 g, yield 85.5%). ##STR9##

Workup

  1. temperatureis heated to 210°-215° C. on an oil bath for 45 minutes
  2. temperatureto cool
  3. extractionThe mixture is extracted with water and diethyl ether
  4. customThe ether layer is separated
  5. washwashed
  6. additionwith dilute hydrochrolic acid
  7. dry with materialwater, dried
  8. concentrationconcentrated
  9. washeluted with a mixture of acetonitrile and dichloromethane (1:9 to 1:4)

Sources & evidence

ORD record
ord-1db2b2d84a9744a58541558ebe76fe18
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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