Ethanol → HCID 18544227, compound

HRID 1268145Notes

Reaction equation

HRID 1268145 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=O)[CH2:7][CH:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[BH4-].[Na+].C(O)C.O>C(OCC)C.CS(C)=O.CCCCCC.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH2:8][CH:7]=[C:6]2[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 2810159HCID 2810159, compoundHCID 4311764Sodium borohydride

Product 1

HCID 18544227HCID 18544227, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 21226440Methylenechloride HexaneSolvent

Procedure

2,3-Dihydro-5,6-dimethoxy-3-phenyl-1H-inden-1-one (8.010 g, 29.85 mmol) and NaBH4 (1.355 g, 35.82 mmol) were stirred in diethylether (100 mL) at 0° C. as ethanol (100 mL) was added slowly. The mixture was allowed to stir at room temperature for 24 hours. The mixture was then poured onto crushed ice and then washed with diethylether (3×100 mL). The organic fractions were then dried over MgSO4, filtered, and the volatile components were removed under vacuum resulting in the isolation of a yellow solid. This solid was refluxed in anhydrous DMSO (150 mL) for 5 hours and then cooled to room temperature. The mixture was poured onto crushed ice and the total volume was diluted to 500 mL using H2O. This mixture was then washed using diethylether (5×100 mL). The organic fractions were then combined, washed with H2O (1×100 mL) and then dried over MgSO4. The mixture was filtered and the volatile components were removed resulting in the isolation of a dark red oil. Chromatography of the oil on silica gel using hexane/CH2Cl2 (1/1 vol) as the diluent resulted in the isolation of the 5,6-dimethoxy-3-phenyl-1H-indene as a yellow microcrystalline solid (4.91 g, 65.2 percent yield).

Workup

  1. additionwas added slowly
  2. additionThe mixture was then poured
  3. customonto crushed ice
  4. washwashed with diethylether (3×100 mL)
  5. dry with materialThe organic fractions were then dried over MgSO4
  6. filtrationfiltered
  7. customthe volatile components were removed under vacuum
  8. customresulting in the isolation of a yellow solid
  9. temperaturecooled to room temperature
  10. additionThe mixture was poured
  11. customonto crushed ice
  12. additionthe total volume was diluted to 500 mL
  13. washThis mixture was then washed
  14. washwashed with H2O (1×100 mL)
  15. dry with materialdried over MgSO4
  16. filtrationThe mixture was filtered
  17. customthe volatile components were removed
  18. customresulting in the isolation of a dark red oil

Sources & evidence

ORD record
ord-249598bd14a940ed9ac8f1ce0a301a7b
Source dataset
uspto-grants-2003_04
Patent number
US06555634B1

Reaction notes

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