Pyridine → HCID 19828473, compound

HRID 1494524Notes

Reaction equation

HRID 1494524 reaction equation
[CH3:1][C:2]1([CH3:22])[O:7][CH2:6][C:5]2[C:8]([CH:13](O)[C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[CH:9][N:10]=[C:11]([CH3:12])[C:4]=2[O:3]1.N1C=CC=CC=1.S(Cl)([Cl:31])=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:22])[O:7][CH2:6][C:5]2[C:8]([CH:13]([Cl:31])[C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[CH:9][N:10]=[C:11]([CH3:12])[C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 11529834(+/-)-4-Chlorophenyl-5-[(3,4-isopropylidine)-2-methylpyridine]methanol

Product 1

HCID 19828473HCID 19828473, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

88 mg (0.275 mmole) of (+)-2,2,8-trimethyl-5-(4-chloro-α-hydroxybenzyl)-pyrido-[4,3-e]-1,3-dioxane are poured into a 5 ml flask, dissolved in 1 ml of methylene chloride and the flask is sealed under an atmosphere of nitrogen. 22 μl (0.27 mmole) of anhydrous pyridine are injected via a glass syringe. 36 μl (0.54 mmole) of thionyl chloride are then added dropwise. At disappearance (2 hours later) of the starting material (checked by TLC), the solvent is evaporated off under reduced pressure.

Workup

  1. customthe flask is sealed under an atmosphere of nitrogen
  2. customAt disappearance (2 hours later) of the starting material (checked by TLC), the solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-475ca8ea1e1a4280a2598f4fd0196dd1
Source dataset
uspto-grants-1991_06
Patent number
US05026855

Reaction notes

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