Sulfuric Acid → HCID 15637840, compound

HRID 901995Notes

Reaction equation

HRID 901995 reaction equation
[O:1]1[CH:11]2[CH:2]1[CH2:3][C:4]1[C:9]([CH2:10]2)=[CH:8][CH:7]=[CH:6][CH:5]=1.[N-:12]=[N+:13]=[N-:14].[Na+].S(=O)(=O)(O)O>CS(C)=O.C(OCC)(=O)C>[N:12]([C@@H:11]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[OH:1])=[N+:13]=[N-:14]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 108880512,3-Epoxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 15637840HCID 15637840, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2,3-epoxy-1,2,3,4-tetrahydronaphthalene (prepared in the manner disclosed in U.S. Pat. No. 4,076,843, 1.7 g, 11.6 mmol) in dimethyl sulfoxide (20 mL) at room temperature under nitrogen was added sodium azide (6.7 g, 0.10 mol) and concentrated sulfuric acid (0.2 mL). After 60 h, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with brine three times, dried over anhydrous magnesium sulfate, and concentrated under vacuum to yield a residue. The residue was purified by silica gel chromatography (10% ethyl acetate in hexane was used) to obtain the title compound (0.43 g, 38%) and recovered starting material. 1H NMR (400 MHz, CDCl3) δ 7.07-7.18 (m, 4H), 3.92 (m, 1H), 3.73 (m, 1H), 3.22 (m, 2H), 2.87 (m, 2H), 2.35 (s, 1H).

Workup

  1. washThe organic layer was washed with brine three times
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customto yield a residue
  5. customThe residue was purified by silica gel chromatography (10% ethyl acetate in hexane was used)

Sources & evidence

ORD record
ord-8a5e3d4b5063422e9a2db5092e9f0b7b
Source dataset
uspto-grants-2008_04
Patent number
US07365061B2

Reaction notes

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