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

HRID 1084882Notes

Reaction equation

HRID 1084882 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. customto rise to 25° C. in the course
  2. extractionis extracted several times
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d8645576abe4e09820e7d1c26c874c9
Source dataset
uspto-grants-1991_04
Patent number
US05006530

Reaction notes

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