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

HRID 542996Notes

Reaction equation

HRID 542996 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].CN([S+](N(C)C)N(C)C)C.C[Si-](F)(F)(C)C.OP([O-])(O)=O.[K+].[OH2:40].[CH2:41]1[CH2:45][O:44][CH2:43][CH2:42]1>C(#N)C.CCOCC>[CH3:41][CH:42]([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

8

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 117679-NitroanthraceneHCID 516951Monobasic potassium phosphateHCID 9795567Tris(dimethylamino)sulfonium difluorotrimethylsilicate

Product 1

HCID 13507922Methyl alpha-Methyl-9-nitro-9,10-dihydroanthracene-10-acetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.757 g (3.39 mmol) of 9-nitroanthracene and 0.663 mL (3.56 mmol) of MTS in 20 mL of anhydrous THF was added 0.941 g (3.42 mmol) of TASF in 2 mL of anhydrous acetonitrile at -78° C. The mixture was stirred for 24 hr. at -78° C. Then, ten mL of saturated KH2PO4 and 20 mL of water were added, the mixture was warmed to room temperature, and the product was extracted into ether. The combined ether extract was washed with water, dried, and concentrated. The major product, 0.491 g (56%), was isolated by column chromatography on silica using 20° ether/hexane as the solvent. Addition of small amount of ether to the major fraction yielded a light yellow solid. The product was analyzed by ultraviolet absorption, infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry.

Workup

  1. customat -78° C
  2. extractionthe product was extracted into ether
  3. extractionThe combined ether extract
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe major product, 0.491 g (56%), was isolated by column chromatography on silica using 20° ether/hexane as the solvent
  8. customyielded a light yellow solid
  9. customThe product was analyzed by ultraviolet absorption

Sources & evidence

ORD record
ord-bd691a6101bf48498f40201522791a6d
Source dataset
uspto-grants-1987_04
Patent number
US04659862

Reaction notes

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