Sodium Hydroxide → HCID 86716209, compound

HRID 512182Notes

Reaction equation

HRID 512182 reaction equation
[F:1][C:2]1([F:17])[CH2:7][CH2:6][C:5]([C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[N:14][CH:15]=2)([C:8]#N)[CH2:4][CH2:3]1.[OH-:18].[Na+].C[OH:21].O>>[F:1][C:2]1([F:17])[CH2:7][CH2:6][C:5]([C:10]2[CH:11]=[N:12][C:13]([CH3:16])=[N:14][CH:15]=2)([C:8]([OH:21])=[O:18])[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 22242641Methanol--water (1/1)HCID 86716210HCID 86716210, compound

Product 1

HCID 86716209HCID 86716209, compoundYield 92%

Conditions

Temperature
100 °C

Procedure

To a mixture of 4,4-difluoro-1-(2-methylpyrimidin-5-yl)cyclohexanecarbonitrile (1.2 g, 5.1 mmol) in MeOH/H2O (20 mL, 1:1) was added NaOH (612 mg, 15.3 mmol) and heated to 100° C. overnight. The MeOH was removed in vacuo. The aqueous layer was extracted with EtOAc (3×30 mL) and the organic layers was discarded. The aqueous layer was adjusted pH to 3˜4 with 3N HCl and extracted with EtOAc (3×30 mL). The organic layer was dried over Na2SO4 and concentracted to give 4,4-difluoro-1-(2-methylpyrimidin-5-yl)cyclohexanecarboxylic acid (1.2 g, yield: 92%). 1H NMR (CDCl3 400 MHz): δ8.81 (s, 2H), 2.80-2.60 (m, 5H), 2.20-2.00 (m, 6H).

Workup

  1. customThe MeOH was removed in vacuo
  2. extractionThe aqueous layer was extracted with EtOAc (3×30 mL)
  3. extractionextracted with EtOAc (3×30 mL)
  4. dry with materialThe organic layer was dried over Na2SO4

Sources & evidence

ORD record
ord-07d4b37ea4724feeae6c32f226b85b8d
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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