Water → Ethyl 2,6-diisopropyl-4-(4-fluorophenyl)-5-methoxymethylpyridine-3-carboxylate

HRID 1681253Notes

Reaction equation

HRID 1681253 reaction equation
[CH3:1]I.[H-].[Na+].[CH:5]([C:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:11]([CH2:26][OH:27])=[C:10]([CH:28]([CH3:30])[CH3:29])[N:9]=1)([CH3:7])[CH3:6].O>O1CCCC1>[CH:5]([C:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[C:11]([CH2:26][O:27][CH3:1])=[C:10]([CH:28]([CH3:29])[CH3:30])[N:9]=1)([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10291957Ethyl 2,6-Diisopropyl-4-(4-fluorophenyl)-3-hydroxymethylpyridine-5-carboxylate

Product 1

HCID 18926957Ethyl 2,6-diisopropyl-4-(4-fluorophenyl)-5-methoxymethylpyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.57 ml (9.2 mmol) of methyl iodide and, at -50° C. 327 mg (10.9 mmol) of 80% strength sodium hydride are added under a nitrogen atmosphere to 3 g (8.4 mmol) of the compound from Example 4 in 100 ml of dry tetrahydrofuran. The mixture is stirred for 2 hours and the temperature is allowed to rise to 25° C. in the course of this. Water is cautiously added to the mixture and it is extracted several times using ether, and the organic phase is dried over sodium sulphate and concentrated in vacuo.

Workup

  1. customat -50° C
  2. customto rise to 25° C. in the course
  3. extractionis extracted several times
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36e4db81547149bd8ab748ab2727724c
Source dataset
uspto-grants-1992_12
Patent number
US05169857

Reaction notes

Loading…