Water → 2-(1,4-Dioxaspiro(4.5)decan-8-yl)ethyl azide

HRID 2193116Notes

Reaction equation

CN(C)C=O.CS(O[CH2:11][CH2:12][CH:13]1[CH2:22][CH2:21][C:16]2([O:20][CH2:19][CH2:18][O:17]2)[CH2:15][CH2:14]1)(=O)=O.[N-:23]=[N+:24]=[N-:25].[Na+].O>C(OCC)(=O)C>[O:20]1[C:16]2([CH2:21][CH2:22][CH:13]([CH2:12][CH2:11][N:23]=[N+:24]=[N-:25])[CH2:14][CH2:15]2)[O:17][CH2:18][CH2:19]1

Participants

Conditions

Temperature: 47.5 °C

Procedure

To 10 mL of an N,N-dimethylformamide solution containing 1.4 g of 2-(1,4-dioxaspiro(4.5)decan-8-yl)ethyl methanesulfonate, 0.45 g of sodium azide was added at room temperature, and the mixture was stirred at 45 to 50° C. for 1 hour and 30 minutes. Thereto was further added 70 mg of sodium azide, and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and then dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=4:1] to obtain 1.0 g of a colorless oily substance, 2-(1,4-dioxaspiro(4.5)decan-8-yl)ethyl azide.

Workup

additionwas added at room temperature
stirringthe mixture was stirred at the same temperature for 2 hours
temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
washwashed with an aqueous saturated sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe residue thus obtained
customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=4:1]

Sources & evidence

ORD record: ord-32142d530da448319799931ad1ecef36
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329694B2

Reaction notes

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