Water → HCID 11084333, compound

HRID 743933Notes

Reaction equation

HRID 743933 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 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of sodium ethoxide (20.0 g, 0.20 mole) in ethanol (600 ml), a solution of 2-tetralone (42.4 g, 0.29 mole) in ethanol (100 ml) was added dropwise at 0° C. with stirring, then p-toluenesulfonylazide (59.2 g, 0.3 mole) was added dropwise at -15° C. or below to the mixture and reacted with stirring for 3 hours at -10° to 0° C. The reaction mixture was poured into H2O (1 l), extracted with methylene chloride (500 ml×2), the organic layer separated was washed with H2O (500 ml×3), dried over anhydrous MgSO4 and evaporated. The oily residue (72 g) was chromatographed on silica gel (Wakogel C-200) with n-hexane-n-hexane/methylene chloride (1/1) as eluent and recrystallized from n-hexane to afford 6.0 g of 1-diazo-2-tetralone as yellow crystals. m.p. 42.5°-44.2° C.

Workup

  1. customreacted
  2. stirringwith stirring for 3 hours at -10° to 0° C
  3. extractionextracted with methylene chloride (500 ml×2)
  4. customthe organic layer separated
  5. washwas washed with H2O (500 ml×3)
  6. dry with materialdried over anhydrous MgSO4
  7. customevaporated
  8. customThe oily residue (72 g) was chromatographed on silica gel (Wakogel C-200) with n-hexane-n-hexane/methylene chloride (1/1) as eluent
  9. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-19fb1ba979314da09e671ca9b56d6a52
Source dataset
uspto-grants-1996_09
Patent number
US05558971

Reaction notes

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