Sodium Hydroxide → HCID 86690088, compound

HRID 520368Notes

Reaction equation

HRID 520368 reaction equation
[OH-].[Na+].[F:3][C:4]1([F:17])[CH2:9][CH2:8][C:7]([CH2:15][F:16])([C:10]([O:12]CC)=[O:11])[CH2:6][CH2:5]1>C1COCC1.CO>[F:3][C:4]1([F:17])[CH2:5][CH2:6][C:7]([CH2:15][F:16])([C:10]([OH:12])=[O:11])[CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86690089HCID 86690089, compound

Product 1

HCID 86690088HCID 86690088, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1 N NaOH (0.994 mL, 0.994 mmol) was added to a solution of ethyl 4,4-difluoro-1-(fluoromethyl)cyclohexanecarboxylate (73.6 mg, 0.331 mmol) in THF (1 mL) and MeOH (1 ml) and the mixture was stirred at rt for 3-4 h. The reaction mixture was acidified and extracted with EtOAc, washed with brine and dried (MgSO4). Evaporation of the solvent afforded Cap-7 as a beige solid. 1H NMR (400 MHz, CHLOROFORM-d) δ 4.38 (d, J=47.1 Hz, 2H), 2.30-2.16 (m, 2H), 2.11-1.98 (m, 2H), 1.96-1.76 (m, 2H), 1.65-1.51 (m, 2H).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customEvaporation of the solvent
  5. customafforded Cap-7 as a beige solid

Sources & evidence

ORD record
ord-dde88f7c459f4121a8ea32266f42b228
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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