Sodium Azide → Methyl 11-azidoundecanoate

HRID 2039757Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].[N-:16]=[N+:17]=[N-:18].[Na+]>CS(C)=O>[CH3:15][O:14][C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:16]=[N+:17]=[N-:18]

Participants

Conditions

Temperature: 66 °C

Procedure

A mixture of 13.3 g of methyl 11-bromoundecanoate and 3.12 g of sodium azide in 50 mL of DMSO was heated at 66° C. under nitrogen for 2 days. The reaction mixture was cooled down and mixed with 200 mL of ice water. The aqueous layer was extracted with ether (1×100 mL, subsequently 3×50 mL). The organic layers were combined, washed twice with 25 mL of brine and dried over Na2SO4. Removal of the solvents in vacuo gave 11.2 g of a yellow oil. Purification by column chromatography (silica gel; petroleum ether (40-60° C.)/ether=9:1 (v/v)) gave 10.94 g of the pure product as a colorless oil, which was stored at 4° C. to prevent degradation. 1H NMR (300 MHz, CDCl3): δ 3.65 (s, 3H); 3.24 (t, 2H, J=7.0 Hz); 2.29 (t, 2H, J=7.5 Hz); 1.65-1.53 (m, 2H); 1.42-1.21 (m, 14H) ppm. 13C NMR (75 MHz, CDCl3): δ 174.24; 51.44; 51.37; 34.04; 29.35; 29.27; 29.15; 29.07; 28.80; 26.66; 24.89 ppm. IR (neat, cm−1): 2929 (m); 2856 (m); 2096 (s); 1741 (s).

Workup

temperatureThe reaction mixture was cooled down
extractionThe aqueous layer was extracted with ether (1×100 mL, subsequently 3×50 mL)
washwashed twice with 25 mL of brine
dry with materialdried over Na2SO4
customRemoval of the solvents in vacuo

Sources & evidence

ORD record: ord-e24eb4664add4b33a1e9e6804d7fa26e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580810B2

Reaction notes

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