Sodium Hydroxide → 1773508-66-9

HRID 920793Notes

Reaction equation

HRID 920793 reaction equation
[F:1][C:2]1([F:17])[CH2:5][C:4]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)([C:6]([O:8]C)=[O:7])[CH2:3]1.[OH-].[Na+]>CO.O.C1COCC1>[F:17][C:2]1([F:1])[CH2:3][C:4]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)([C:6]([OH:8])=[O:7])[CH2:5]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 118061145HCID 118061145, compound

Product 1

HCID 1054874861773508-66-9Yield 66.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Intermediate 308D (400 mg, 1.638 mmol) in MeOH (5 mL), water (2 mL) and THF (2 mL) was added NaOH (197 mg, 4.91 mmol) and stirred for 12 h at RT. The reaction mixture was concentrated under vacuo and the pH of the residue was adjusted to 2.0 using 1.5 N HCl and the compound was extracted with ethyl acetate (3×10 mL) The combined organic layer was dried over Na2SO4, filtered and the filtrate concentrated under reduced pressure to afford Intermediate 308E as a pale yellow solid (250 mg, 66%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.03 (bs, 1H), 7.33-7.43 (m, 2H), 7.21 (m, 2H), 3.32-3.37 (m, 2H), 2.99-3.15 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuo
  2. extractionthe compound was extracted with ethyl acetate (3×10 mL) The combined organic layer
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-2b4bb4c695b64b0195bfc9410b3d04b1
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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