Sodium Hydroxide → 1773508-48-7

HRID 920781Notes

Reaction equation

HRID 920781 reaction equation
[F:1][C:2]1([F:14])[CH2:5][C:4]([CH2:12][F:13])([C:6]([O:8]C(C)C)=[O:7])[CH2:3]1.[OH-].[Na+]>C(O)C>[F:1][C:2]1([F:14])[CH2:3][C:4]([CH2:12][F:13])([C:6]([OH:8])=[O:7])[CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118062418HCID 118062418, compound

Product 1

HCID 1180626221773508-48-7Yield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of Intermediate 302D (0.25 g, 1.189 mmol) in ethanol (5 mL) was added NaOH (1.189 mL, 5.95 mmol, 5 M in water) and the reaction mixture was stirred at RT for 8 h. The reaction mixture was concentrated in vacuo, dissolved in water and extracted with diethyl ether. The pH of the aq. solution was adjusted to 7 using a 2N aq. solution of HCl and extracted with DCM (3×10 mL) The combined organic layer was dried over Na2SO4, filtered, and the filtrate concentrated to afford Intermediate 302E as a pale yellow liquid (0.12 g, 60%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.02-13.40 (br. s., 1H), 4.53-4.76 (m, 2H), 2.95 (q, J=13.22 Hz, 2H), 2.59-2.78 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water
  3. extractionextracted with diethyl ether
  4. extractionextracted with DCM (3×10 mL) The combined organic layer
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-00c68cb7ad3946d09b8eb93e1d10405d
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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