Sodium Azide → 4-(Azidomethyl)-2,2-dimethyl-1,3-dioxolane

HRID 1157082

Reaction equation

CC1C=CC(S(O[CH2:12][CH:13]2[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]2)(=O)=O)=CC=1.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C>[N:20]([CH2:12][CH:13]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14]1)=[N+:21]=[N-:22]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (5.73 g, 20.00 mmol) in DMF (40 mL) was added sodium azide (2.6 g, 40.00 mmol) and the reaction mixture was stirred at 80° C. for 18 hr. The solvent was evaporated under reduced pressure, diluted with water (100 mL) and extracted 3 times with ethyl acetate (3×75 mL), which was consecutively washed with H2O (100 mL), brine (100 mL) and finally dried over MgSO4. The solvent was removed under vacuum to afford 2.2 g of 13 as brown oil (76% yield). 1H NMR (CDCl3, 400 MHz) δ: 4.21-4.27 (m, 1H), 4.02 (dd, J=6.4, 8.4 Hz, 1H), 3.74 (dd, J=6.0, 8.4 Hz, 1H), 3.36 (dd, J=4.8, 12.8 Hz, 1H), 3.26 (dd, J=5.6, 12.8 Hz, 1H), 1.43 (s, 3H), 1.33 (s, 3H).

Workup

customThe solvent was evaporated under reduced pressure
additiondiluted with water (100 mL)
extractionextracted 3 times with ethyl acetate (3×75 mL), which
washwas consecutively washed with H2O (100 mL), brine (100 mL)
dry with materialfinally dried over MgSO4
customThe solvent was removed under vacuum

Sources & evidence

ORD record: ord-9d06994532b344cba44c54d3aba6899e
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807394B2

Linked notes

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