Sodium Chloride → 7-Dimethylaminomethyl-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

HRID 2051415Notes

Reaction equation

HRID 2051415 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]2[C:3]=1[CH:4]1[CH:9]([C:10]2=[O:16])[CH2:8][CH2:7][CH2:6][CH2:5]1.C(OC(=O)C)(=O)C.[CH3:24][N:25]([CH2:27]N(C)C)[CH3:26].[Cl-].[Na+]>>[CH3:24][N:25]([CH2:27][C:13]1[C:12]([OH:15])=[C:11]2[C:3]([CH:4]3[CH:9]([C:10]2=[O:16])[CH2:8][CH2:7][CH2:6][CH2:5]3)=[C:2]([CH3:1])[CH:14]=1)[CH3:26]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 5829N,N,N',N'-TetramethylmethanediamineHCID 7918Acetic AnhydrideHCID 15157186HCID 15157186, compound

Product 1

HCID 151571967-Dimethylaminomethyl-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Conditions

Temperature
90 °C

Procedure

A mixture of 25 g of 5-methyl-8-hydroxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone, 62.5 ml of acetic anhydride and 18.88 ml of bisdimethylaminomethane was stirred with heating at 90° C. for 2 hours. The reaction mixture was left to stand for cooling and then to the reaction mixture was added saturated aqueous sodium chloride solution, followed by extraction with dichloromethane. The organic layer was dried with magnesium sulfate and then the solvent was distilled off. The residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:10) to obtain 14.37 g of 7-dimethylaminomethyl-8-hydroxy-5-methyl-1,2,3,4,4a,9a-hexahydro-9-fluorenone.

Workup

  1. waitThe reaction mixture was left
  2. temperaturefor cooling
  3. extractionfollowed by extraction with dichloromethane
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:10)

Sources & evidence

ORD record
ord-9415ffc1ed9d4c05b75fd7d43c41738c
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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