Lithium Hydroxide → HCID 57438727, compound

HRID 2354510Notes

Reaction equation

HRID 2354510 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]([F:10])[F:9].[OH-:11].[Li+].[CH3:13][OH:14].O1C[CH2:18][CH2:17][CH2:16]1.[OH2:20]>>[CH3:16][C:17]([O:20][C:6]1[CH:7]=[CH:2][C:3]([CH:8]([F:10])[F:9])=[CH:4][N:5]=1)([CH3:18])[C:13]([OH:14])=[O:11]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 21892291Methanol tetrahydrofuran waterHCID 57438728HCID 57438728, compound

Product 1

HCID 57438727HCID 57438727, compound

Procedure

The title compound (1.6 g) was prepared from 4-chloro-3-difluoromethylpyridine (3.0 g) following the procedure described for Reference Example 15 with the following modifications. The ester intermediate was purified by flash column chromatography on silica gel eluting with 0 to 10% ether in hexane. The hydrolysis of the ester to the title compound was effected with lithium hydroxide in methanol/tetrahydrofuran/water. 1H NMR (500 MHz, CD3OD): δ 8.22 (d, 1H), 7.82 (dd, 1H), 6.88 (d, 1H), 6.77 (t, 1H), 1.64 (s, 6H).

Workup

  1. customThe ester intermediate was purified by flash column chromatography on silica gel eluting with 0 to 10% ether in hexane
  2. customThe hydrolysis of the ester to the title compound

Sources & evidence

ORD record
ord-78916605d1714e119d0747c031da009b
Source dataset
uspto-grants-2010_07
Patent number
US07754188B2

Reaction notes

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