Water → HCID 118062710, compound

HRID 920791Notes

Reaction equation

HRID 920791 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:16]#N)[CH2:11][C:10]([O:14][CH3:15])([O:12][CH3:13])[CH2:9]2)=[CH:4][CH:3]=1.[OH-:18].[Na+].[OH2:20]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:16]([OH:20])=[O:18])[CH2:11][C:10]([O:14][CH3:15])([O:12][CH3:13])[CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 64905840HCID 64905840, compound

Product 1

HCID 118062710HCID 118062710, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Intermediate 308A (1.4 g, 5.95 mmol) in ethanol (20 mL) and H2O (20 mL) was added a10% aq. solution of NaOH (10 mL, 5.95 mmol) and the reaction mixture was heated at reflux for 12 h. The reaction mixture was concentrated under reduced pressure to afford Intermediate 308B (1.0 g, 66% yield) as a gummy solid. The crude product was used in the subsequent reaction without purification. 1H NMR (400 MHz, chloroform-d) δ ppm 7.45 (dd, J=8.94, 5.05 Hz, 2H), 7.09 (t, J=8.66 Hz, 2H), 2.82-3.0 (m, 8H), 2.64-2.72 (m, 2H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 12 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-319147ae9e3a472e9b9a6b8dd735d44c
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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