Sodium Azide → HCID 19390014, compound

HRID 1757220Notes

Reaction equation

HRID 1757220 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][CH:6]1[CH2:23][CH2:22][C:9]2([CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][C:17]3[CH:21]=[CH:20][O:19][CH:18]=3)[CH2:11][CH2:10]2)[CH2:8][CH2:7]1.[N-:24]=[N+:25]=[N-:26].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C1C=CC=CC=1.C(OCC)(=O)C>[N:24]([CH:2]([CH2:3][OH:1])[CH2:4][O:5][CH:6]1[CH2:23][CH2:22][C:9]2([CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][C:17]3[CH:21]=[CH:20][O:19][CH:18]=3)[CH2:11][CH2:10]2)[CH2:8][CH2:7]1)=[N+:25]=[N-:26]

Participants

7

Reactant 2

HCID 33557Sodium AzideHCID 15234851HCID 15234851, compound

Product 1

HCID 19390014HCID 19390014, compoundYield 80.8%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.12 g of 9-(oxiranylmethoxy)-3-(2-(3-furyl)ethyl)-spiro[5.5]-undecane (prepared as intermediate in Ex. 21), 0.130 g of sodium azide and 0.030 g of tetrabutylammonium hydrogen sulfate in 1.5 ml of water and 1.5 ml of benzene was vigorously stirred at reflux temperature for 48 hrs. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, the organic phase washed with water several times, dried on sodium sulfate and evaporated to dryness. The residue was purified by chromatography (SiO2 ; n-hexane/diethylether 50/50), to give 0.110 g of 9-(2-azido-3-hydroxypropoxy)-3-(2-(3-furyl)ethyl)-spiro[5.5]-undecane as brown foam. [TLC: Rf=0.48 (SiO2 plates, diethylether/n-hexane 70/30). PG,28 1H-NMR (300 MHz, CDCl3, ppm from TMS): 7.35 (1H, m), 7.20 (1H, m), 6.23 (1H, m), 4.00-3.80 (1H, m), 3.55-3.20 (5H, m), 2.42 (2H, t), 1.90-0.80 (19H, m)].

Workup

  1. temperatureat reflux temperature for 48 hrs
  2. washthe organic phase washed with water several times
  3. customdried on sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography (SiO2 ; n-hexane/diethylether 50/50)

Sources & evidence

ORD record
ord-6f8d1ca73a1f4926be7f6db14e7f9f9a
Source dataset
uspto-grants-1995_08
Patent number
US05444082

Reaction notes

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