Water → HCID 11084333, compound

HRID 1779275Notes

Reaction equation

HRID 1779275 reaction equation
[O-]CC.[Na+].[CH2:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:15].C1(C)C=CC(S([N:25]=[N+:26]=[N-])(=O)=O)=CC=1.O>C(O)C>[N+:25](=[C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:15])=[N-:26]

Participants

6

Reactant 4

HCID 962WaterHCID 13661p-Toluenesulfonyl azideHCID 682662-TetraloneHCID 2723922Sodium ethoxide

Product 1

HCID 11084333HCID 11084333, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of sodium ethoxide (4.68 g) in ethanol (150 ml), a solution of 2-tetralone (5.0 g, 34 mmole) in ethanol (10 ml) was added dropwise at 0° C., followed by the dropwise addition of p-toluenesulfonylazide (6.9 g, 35 mmole) obtained in Synthesis Example 7, (1), at -15° C. The resultant mixture was poured into cold H2O (350 ml), extracted with methylene chloride (250 ml×2), and the organic layer was washed with H2O (200 ml), dried over anhydrous MgSO4 and evaporated in vacuo. The resultant purplish-red crystals (5.2 g) were chromatographed on silica gel (Wakogel C-200) with n-hexane/methylene chloride [7/1→5/1→3/1 (v/v)] as eluent to give 2.3 g of the desired product as orange crystals having a melting point of 41.5°-43.5° C.

Workup

  1. customobtained in Synthesis Example 7, (1), at -15° C
  2. extractionextracted with methylene chloride (250 ml×2)
  3. washthe organic layer was washed with H2O (200 ml)
  4. dry with materialdried over anhydrous MgSO4
  5. customevaporated in vacuo
  6. customThe resultant purplish-red crystals (5.2 g) were chromatographed on silica gel (Wakogel C-200) with n-hexane/methylene chloride [7/1→5/1→3/1 (v/v)] as eluent

Sources & evidence

ORD record
ord-9ff5faa7f90a479e93354a1b2e566da6
Source dataset
uspto-grants-1997_05
Patent number
US05627006

Reaction notes

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