Sodium Bicarbonate → HCID 57682927, compound

HRID 494937Notes

Reaction equation

HRID 494937 reaction equation
[OH:1][CH:2]([CH2:17][OH:18])[CH2:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][CH2:8][C:9]2=O.OC1C=C2C(=CC=1)C(=O)CCC2.Cl.[O:32]([NH2:34])[CH3:33].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O1CCCC1.CO>[CH3:33][O:32][N:34]=[C:9]1[C:10]2[C:5](=[C:4]([CH2:3][CH:2]([OH:1])[CH2:17][OH:18])[C:13]([O:14][CH3:15])=[CH:12][CH:11]=2)[CH2:6][CH2:7][CH2:8]1

Participants

9

Reactant 5

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneHCID 57682846HCID 57682846, compound

Product 1

HCID 57682927HCID 57682927, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

200 mg of 5-(2,3-dihydroxypropyl)-6-methoxy-1-tetralone synthesized from 6-hydroxy-1-tetralone according to the methods described in Example 7, (1)-(4), was dissolved in a mixed solution consisting of 5 ml of methanol and 3 ml of tetrahydrofuran. Thereafter, 401 mg of methoxylamine hydrochloride and 394 mg of sodium acetate were added to the reaction solution, and the obtained mixture was then stirred at room temperature. After completion of the reaction, a saturated sodium bicarbonate aqueous solution and ethyl acetate were added to the reaction solution, so as to separate an organic layer. The obtained organic layer was washed with a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure, so as to obtain 183 mg of 5-(2,3-dihydroxypropyl)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one O-methyloxime. The subject compound was obtained from the thus obtained compound according to the method described in Example 1, (4).

Workup

  1. dissolutionwas dissolved in a mixed solution
  2. customAfter completion of the reaction
  3. customso as to separate an organic layer
  4. washThe obtained organic layer was washed with a saturated sodium bicarbonate aqueous solution
  5. dry with materiala saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate
  6. customAfter removing the drying agent
  7. filtrationby filtration
  8. concentrationthe organic layer was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-e3e9651e51954128b427738ba0bceceb
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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