Water → Methyl alpha,alpha-Dimethyl-9-nitro-9,10-dihydroanthracene-10-acetate

HRID 1165999Notes

Reaction equation

HRID 1165999 reaction equation
[N+:1]([C:4]1[C:5]2[C:10]([CH:11]=[C:12]3[C:17]=1[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2)([O-:3])=[O:2].CSS(C)(=O)=O.CN([S+](N(C)C)N(C)C)C.[CH3:34][Si-](F)(F)(C)C.[OH2:40].[CH2:41]1[CH2:45][O:44][CH2:43][CH2:42]1>C(#N)C>[CH3:34][C:42]([CH3:41])([CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([N+:1]([O-:3])=[O:2])[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=2)[C:43]([O:44][CH3:45])=[O:40]

Participants

7

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 117679-NitroanthraceneHCID 18064S-Methyl methanethiosulfonateHCID 9795567Tris(dimethylamino)sulfonium difluorotrimethylsilicate2×

Product 1

HCID 13507921Methyl alpha,alpha-Dimethyl-9-nitro-9,10-dihydroanthracene-10-acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.115 g (5 mmol) of 9-nitroanthracene and 1.01 mL (5 mmol) of MMTS in 20 mL of anhydrous THF was treated with 1.375 g (5 mmol) of TASF dissolved in 3 mL of acetonitrile at -78° C. After addition of TASF had been completed, the reaction mixture was brought to -10° C. and stirred for 1 hr. Ten mL of water was then added, the mixture was warmed to room temperature, and the product was extracted into ether. The organic layer was washed with saturated sodium chloride solution, dried and concentrated. The melting point was 159° to 163° C. (dec). The product material was analyzed by ultraviolet absorption, infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry.

Workup

  1. customwas brought to -10° C.
  2. extractionthe product was extracted into ether
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customThe product material was analyzed by ultraviolet absorption

Sources & evidence

ORD record
ord-6008d7d60fab4ead829b91695ac61d94
Source dataset
uspto-grants-1990_03
Patent number
US04912220

Reaction notes

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