Sodium Hydroxide → HCID 19848788, compound

HRID 2118906Notes

Reaction equation

HRID 2118906 reaction equation
CO[NH:3][CH:4]1[O:28][C:12]2=[CH:13][C:14]([O:16][CH:17]([CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:18])=[CH:15][C:10]3=[C:11]2[CH:6]([CH2:7][C:8]([CH3:30])([CH3:29])[O:9]3)[CH2:5]1.[OH-].[Na+]>CO.[Ni].[Al]>[NH2:3][CH2:4][CH2:5][CH:6]1[C:11]2[C:12]([OH:28])=[CH:13][C:14]([O:16][CH:17]([CH2:19][CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH3:18])=[CH:15][C:10]=2[O:9][C:8]([CH3:29])([CH3:30])[CH2:7]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19848772HCID 19848772, compound

Product 1

HCID 19848788HCID 19848788, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 6336846Nickel aluminideCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

In a stirred flask, under nitrogen, was placed 17.5 g (0.043 mole) 2-methoxyamino-5,5-dimethyl-8-(5-phenyl-2-pentyloxy)-3,3a,4,5-tetrahydro-2H-pyrano[4,3,2-de]benzopyran in 1800 ml methanol. The mixture was warmed to 40° C. and 1080 ml 1N sodium hydroxide was added in portions over ten minutes. The mixture was heated to 55° C. and 20.4 g Raney Alloy (nickel/aluminum 1:1 by weight) was added in portions over ten minutes (foaming!). The resulting mixture was stirred at 55° C. for one hour, allowed to cool to room temperature and the catalyst removed by filtration. The filtrate was evaporated in vacuo to an oil which was combined with water and 6N hydrochloric acid added to adjust the mixture of pH 6-7. The neutralized mixture was extracted with ethyl acetate, the organic layer backwashed with brine, dried (MgSO4), filtered and the solvent evaporated at reduced pressure to provide 16.4 g crude product as an oil.

Workup

  1. customIn a stirred flask, under nitrogen, was placed
  2. temperatureThe mixture was heated to 55° C.
  3. temperatureto cool to room temperature
  4. customthe catalyst removed by filtration
  5. customThe filtrate was evaporated in vacuo to an oil which
  6. additionadded
  7. additionthe mixture of pH 6-7
  8. extractionThe neutralized mixture was extracted with ethyl acetate
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customthe solvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-e2b211e0a21743cea2ebc1c32254e185
Source dataset
uspto-grants-1987_07
Patent number
US04680404

Reaction notes

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