Azidotrimethylsilane → 1,5-Bis-benzyloxy-2-isopropyl-4-azido-benzene

HRID 623664Notes

Reaction equation

[Si]([N:5]=[N+:6]=[N-:7])(C)(C)C.[CH2:8]([O:15][C:16]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19](N)=[CH:18][C:17]=1[CH:31]([CH3:33])[CH3:32])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CC#N>[CH2:8]([O:15][C:16]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:19]([N:5]=[N+:6]=[N-:7])=[CH:18][C:17]=1[CH:31]([CH3:33])[CH3:32])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

tBuONO (2.25 ml, 19 mmol) and TMSN3 (2 ml, 15.2 mmol) were added to a solution of 1,5-bis-benzyloxy-2-isopropyl-4-amino-benzene (1.10 g, 3.18 mmol) in CH3CN (40 ml). The reaction mixture was stirred for 1 hour at 0° C. and for 12 hours at RT. The solvent was evaporated under reduced pressure and the crude reaction mixture was purified by flash chromatography (PE/AcOEt:95/5 to 90/10). The title compound was obtained as a brown solid (890 mg, 75%).

Workup

customThe solvent was evaporated under reduced pressure
customthe crude reaction mixture
customwas purified by flash chromatography (PE/AcOEt:95/5 to 90/10)

Sources & evidence

ORD record: ord-4a2db9f3b66e45c28fb886e4b7e39f5c
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302998B2

Reaction notes

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