9H-Xanthen-9-one, 3-methoxy- → HCID 14966062, compound

HRID 1275528Notes

Reaction equation

HRID 1275528 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13](=O)[C:14]3[C:19]([O:20][C:21]=2[CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3>CCOCC.C1(C)C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C:14]3[C:19]([O:20][C:21]=2[CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3

Participants

5

Reactant 2

HCID 773099H-Xanthen-9-one, 3-methoxy-HCID 21226445Aluminium lithium hydride

Product 1

HCID 14966062HCID 14966062, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of lithium aluminum hydride (0.524 g, 13.8 mmole) in Et2O (30 ml) at 0° was added, dropwise, a solution of xanthone 8 (1 g, 4.42 mmole) in toluene (25 ml). The resulting mixture was stirred at room temperature for 30 min, then refluxed vigorously for 17 hrs. After cooling in an ice bath, the reaction was quenched carefully with EtOAc (1.5 ml), MeOH (1.5 ml) and finally with dilute HCl solution until the aqueous layer was acidic. The reaction mixture was partitioned between 10% EtOAc-hexanes and water. After the organic layer was separated, the aqueous layer was extracted two more times with 10% EtOAc-hexanes. The combined organic layers were washed with saturated NaCl solution, dried over anhydrous Na2SO4 and filtered through a silica gel plus. After concentration of the filtrate, 3-methoxy-9H-xanthene 9 (0.806 g, 86%) was isolated as a slightly yellow solid: m.p. 72-74° C.; 1H NMR (CDCl3): delta 7.13-7.20 (2H, m), 6.98-7.06 (3H, m), 6.58-6.62 (2H, m), 3.97 (2H, s) and 3.79 (3H, s); 1R (CHCl3): 3000, 2935, 2836, 1625, 1596, 1520, 1480, 1455, 1438, 1275, 1227, 1150, 1119, 1092, 1031, 962 and 837 cm-1.

Workup

  1. additionwas added
  2. temperaturerefluxed vigorously for 17 hrs
  3. temperatureAfter cooling in an ice bath
  4. customthe reaction was quenched carefully with EtOAc (1.5 ml), MeOH (1.5 ml) and finally with dilute HCl solution until the aqueous layer
  5. customThe reaction mixture was partitioned between 10% EtOAc-hexanes and water
  6. customAfter the organic layer was separated
  7. extractionthe aqueous layer was extracted two more times with 10% EtOAc-hexanes
  8. washThe combined organic layers were washed with saturated NaCl solution
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationfiltered through a silica gel plus

Sources & evidence

ORD record
ord-b07dbab39984426aafe211b9a443a6c0
Source dataset
uspto-grants-2000_12
Patent number
US06162610

Reaction notes

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