Water → cis-3-Azido-4-(4-bromophenoxy)tetrahydrofuran

HRID 2060827Notes

Reaction equation

CS(O[C@H:6]1[C@H:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH2:9][O:8][CH2:7]1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+].O>CN(C)C=O>[N:19]([C@H:6]1[C@@H:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH2:9][O:8][CH2:7]1)=[N+:20]=[N-:21]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of trans-4-(4-bromophenoxy)tetrahydrofuran-3-yl methanesulfonate (133.2 g, 0.395 mol) in dimethylformamide (3 L) was added sodium azide (192.6 g, 2.96 mol) and the reaction was heated at 110° C. for 66 hours. The reaction was cooled to room temperature and water (12 L) was added. This reaction was carried out a total of three times on the same scale, and the combined batches were extracted with tert-butyl methyl ether. The organic layers were then dried over sodium sulfate and concentrated in vacuo to afford product as a red-brown oil, contaminated with 18% dimethylformamide. Corrected yield: 286.7 g, 1.01 mol, 85%. 1H NMR (400 MHz, CDCl3) δ 3.93-3.97 (m, 2H), 4.00 (m, 1H), 4.09 (dd, J=8.7, 5.8 Hz, 1H), 4.17 (dd, J=10.0, 5.6 Hz, 1H), 4.90 (ddd, J=5.4, 5.4, 4.4 Hz, 1H), 6.83 (d, J=9.1 Hz, 2H), 7.41 (d, J=9.0 Hz, 2H).

Workup

temperatureThe reaction was cooled to room temperature
extractionthe combined batches were extracted with tert-butyl methyl ether
dry with materialThe organic layers were then dried over sodium sulfate
concentrationconcentrated in vacuo
customto afford product as a red-brown oil

Sources & evidence

ORD record: ord-cffaf089215d4d65b7cbf5b05e8e1087
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278457B2

Reaction notes

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