Hydrochloric Acid → HCID 86744453, compound

HRID 1111550Notes

Reaction equation

HRID 1111550 reaction equation
[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([CH3:28])[CH:19]=[C:20]([O:26][CH3:27])[C:21]=4[CH3:25])[CH:16]=3)=O)=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:29]([C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([C:42]([C:44]3[CH:53]=[CH:52][C:51]4[C:46](=[C:47]([CH3:57])[CH:48]=[C:49]([O:55][CH3:56])[C:50]=4[CH3:54])[CH:45]=3)=O)[CH:38]=2)[C:33]=1[CH2:58][CH3:59])(=[O:31])=[O:30])[CH3:2].Cl>[Zn].C(O)(=O)C>[CH2:58]([C:33]1[C:34]2[CH:35]=[CH:36][C:37](=[CH:42][C:44]3[CH:53]=[CH:52][C:51]4[C:46](=[C:47]([CH3:57])[CH:48]=[C:49]([O:55][CH3:56])[C:50]=4[CH3:54])[CH:45]=3)[CH2:38][C:39]=2[CH:40]=[CH:41][C:32]=1[S:29]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][C:9](=[CH:13][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([CH3:28])[CH:19]=[C:20]([O:26][CH3:27])[C:21]=4[CH3:25])[CH:16]=3)[CH:10]=[CH:11][C:12]=2[C:3]=1[CH2:1][CH3:2])(=[O:30])=[O:31])[CH3:59]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid3×HCID 68113351HCID 68113351, compound

Product 1

HCID 86744453HCID 86744453, compoundYield 20.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of 0.43 g (1 mmole) of ethyl 6-[(5,8-dimethyl-6-methoxy-2-naphthyl) carbonyl]-2-naphthylsulfone, described in Example XIX, 10 cm3 of glacial acetic acid and 0.65 g of zinc powder (10 mmoles), is heated at reflux with stirring. There is then slowly added 0.85 cm3 (10 mmoles) of 12N HCl and reflux is maintained for 1 hour. There is again added 0.85 cm3 of 12N HCl and the mixture is stirred for 1 hour, while letting the reaction mixture cool. After the addition of 20 cm3 of 12N HCl, it is extracted with ether (3×30 cm3), washed with water, dried on sodium sulfate and evaporated to dryness. The crude yellow solid is rapidly purified by silica 60 gel chromatography (eluant: dichloromethane), followed by recrystallization in a hexane/acetone mixture. After drying, 160 mg of white needles of ethyl 6-[(5,8-dimethyl-6-methoxy- 2-naphthyl) methylene]-2-naphthylsulfone whose melting point is 166° C. are obtained.

Workup

  1. temperatureis heated
  2. temperatureat reflux
  3. temperatureis maintained for 1 hour
  4. stirringthe mixture is stirred for 1 hour
  5. temperaturecool
  6. extractionis extracted with ether (3×30 cm3)
  7. washwashed with water
  8. customdried on sodium sulfate
  9. customevaporated to dryness
  10. customThe crude yellow solid is rapidly purified by silica 60 gel chromatography (eluant: dichloromethane)
  11. customfollowed by recrystallization in a hexane/acetone mixture
  12. customAfter drying

Sources & evidence

ORD record
ord-6704660637a44cb4b4fdfa147bca6f7e
Source dataset
uspto-grants-1990_12
Patent number
US04980509

Reaction notes

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