Sodium Hydroxide → 1773508-76-1

HRID 920802Notes

Reaction equation

HRID 920802 reaction equation
[CH3:1][C:2]1([C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH2:7][C:4]2([CH2:6][CH2:5]2)[CH2:3]1.[OH-].[Na+]>C1COCC1.O>[CH3:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][C:4]2([CH2:6][CH2:5]2)[CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118062643HCID 118062643, compound

Product 1

HCID 1180625741773508-76-1Yield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of Intermediate 317A (200 mg, 0.868 mmol) in THF (2 mL) and water (1 mL) was added NaOH (104 mg, 2.61 mmol) at RT and the reaction mixture was warmed to 50° C. and stirred for 12 h. The reaction mixture was concentrated under a reduced pressure, the residue was to pH 2 with a 1.5 N aq. solution of HCl and extracted with Et2O (3×15 mL) The combined organic layer was dried over Na2SO4, filtered and the filtrate concentrated to afford Intermediate 317B as a colorless liquid (0.12 g, 99%). 1H NMR (300 MHz, DMSO-d6) δ ppm 12.38-11.71 (m, 1H), 2.68-2.50 (m, 2H), 1.86-1.66 (m, 2H), 1.43 (s, 3H), 0.62-0.19 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated under a reduced pressure
  2. extractionextracted with Et2O (3×15 mL) The combined organic layer
  3. dry with materialwas dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-6e4745c9c5bb4814ae456e5acc0a6425
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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