Pyridinium chloride → HCID 9952162, compound

HRID 429451Notes

Reaction equation

HRID 429451 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[C:22]3[C:17](=[CH:18][C:19]([O:23]C)=[CH:20][CH:21]=3)[O:16][CH2:15][C@H:14]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl.N1C=CC=CC=1>O.C(O)C.ClCCl>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([C@H:13]2[C:22]3[C:17](=[CH:18][C:19]([OH:23])=[CH:20][CH:21]=3)[O:16][CH2:15][C@H:14]2[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 10176127Pyridinium chlorideHCID 69931470HCID 69931470, compound

Product 1

HCID 9952162HCID 9952162, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
152.5 °C

Procedure

A mixture of (±)-cis-4-(4-hexylphenyl)-7-methoxy-3-phenylchromane (0.46 g, 1.15 mmol) and anhydrous pyridine hydrochloride (6.60 g, 57.4 mmol) was heated to 150-155° C. as a melt for 18 hours. The mixture was cooled to room temperature, and the resulting orange coloured wax dissolved in a mixture of water (100 ml), hot ethanol (10 ml) and dichloromethane (100 ml). The organic layer was separated and the aqueous layer further extracted with dichloromethane (3×50 ml). The combined organic layers were washed with saturated sodium chloride, dried over sodium sulfate and evaporated to a dark coloured oil, which was purified by column chromatography on silica gel 60, with 2% methanol in dichloromethane as eluent; giving the title compound as a red oil.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer further extracted with dichloromethane (3×50 ml)
  4. washThe combined organic layers were washed with saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. customevaporated to a dark coloured oil, which
  7. customwas purified by column chromatography on silica gel 60, with 2% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-d6e7928c17564e369c01b80338da1a73
Source dataset
uspto-grants-2001_11
Patent number
US06316494B1

Reaction notes

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