p-Toluenesulfonic acid → HCID 14652778, compound

HRID 1164827Notes

Reaction equation

HRID 1164827 reaction equation
[CH2:1]([C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[C:6]([CH2:20][OH:21])=[C:5]([CH2:22][CH3:23])[N:4]=1)[CH3:2].[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[CH2:1]([C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[C:6]([CH2:20][O:21][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][O:24]2)=[C:5]([CH2:22][CH3:23])[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 14652777HCID 14652777, compound

Product 1

HCID 14652778HCID 14652778, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,6-diethyl-4-(4-fluorophenyl)-5-(hydroxymethyl)-3-pyridinecarboxylic acid, methyl ester (10.0 g, 0.0315 mol), dihydropyran (4.3 ml, 0.0473 mol) and 6.17 g of p-toluene sulfonic acid was stirred (25° C.) for 24 hours, taken up in dichloromethane (400 ml), washed with saturated NaHCO3 (1×170 ml), washed with brine (1×170 ml), dried (MgSO4), and chromatographed on silica (85:15 hexane:ethyl acetate) to yield 11.1 g of the title compound.

Workup

  1. washwashed with saturated NaHCO3 (1×170 ml)
  2. washwashed with brine (1×170 ml)
  3. dry with materialdried (MgSO4)
  4. customchromatographed on silica (85:15 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-2834b4d46424437d86fb9ccbbb7bc6b0
Source dataset
uspto-grants-1990_03
Patent number
US04906624

Reaction notes

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