Potassium Sodium Tartrate → 3,4-Dihydro-2H-1-benzopyran-4-amine

HRID 1269448Notes

Reaction equation

HRID 1269448 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[N:17]O)[CH2:9][CH2:8]1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.O>[O:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]([NH2:17])[CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 44866984H-1-Benzopyran-4-one, 2,3-dihydro-, oximeHCID 21226445Aluminium lithium hydride

Product 1

HCID 49619573,4-Dihydro-2H-1-benzopyran-4-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

LAH (6.35 g, 167 mmol) was suspended in THF (100 mL) at 0° C. A solution of chroman-4-one oxime (10.92 g, 66.92 mmol) in THF (100 mL) was added dropwise. The mixture was heated slowly to reflux for 4 h. The reaction was cooled to RT and added drop-wise to a stirred saturated solution of Rochelle's salt in H2O. The bi-phasic mixture was stirred rapidly at RT for 1 h. The layers were separated and the aqueous layer was extracted with EtOAc until tlc analysis of the aqueous layer showed no evidence of the title compound. The combined organics were dried over MgSO4 and concentrated in vacuo to furnish the crude material, which was purified by flash column chromatography to afford the title compound. MS (APCI pos) 150 (M+H).

Workup

  1. temperatureThe mixture was heated slowly
  2. temperatureto reflux for 4 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc until tlc analysis of the aqueous layer
  5. dry with materialThe combined organics were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto furnish the crude material, which
  8. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-71efbab177ec4774aa281887562097b9
Source dataset
uspto-grants-2007_04
Patent number
US07199244B2

Reaction notes

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