Potassium Hydroxide → HCID 58124952, compound

HRID 1971751Notes

Reaction equation

HRID 1971751 reaction equation
[C:1]([N:5]([CH2:13][CH2:14][C:15]([CH3:20])([CH3:19])[CH2:16][C:17]#[CH:18])[C:6](=[O:12])[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].O1CCOCC1>O>[C:1]([N:5]([CH2:13][CH2:14][C:15]([CH3:20])([CH3:19])[CH2:16][C:17]#[CH:18])[C:6](=[O:12])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 312751,4-DioxaneHCID 58124831HCID 58124831, compound

Product 1

HCID 58124952HCID 58124952, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 250 mg of 24d, 250 mg of KOH, 3 ml of dioxane and 1 ml of water was heated at oil bath at 50° C. for 1 hr. The mixture was poured onto water and extracted once with heptane/ether 1/1. The aqueous phase was acidified with cold 1N HCl to pH3 and extracted with ethyl acetate. The organic extract was once washed with sat. NaCl and dried and concentrated, to give 240 mg of 24e, as colorless oil. NMR (CDCl3) δ 1.00 (s, 6, 2×CH3), 1.50 (s, 9, tertC4H9), 2.00 (t, 1, acetylene), 1.70 (m, 2, CH2), 2.10 (m, 2, CH2), 3.71 (m, 2, CH2).

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted once with heptane/ether 1/1
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas once washed with sat. NaCl
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e8b2d2fc199e41a7b83e3c797871035b
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

Loading…