tert-Butanol → HCID 68089533, compound
Reaction equation
[N+:1]([C:4]1[C:13]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][C:5]=1C(O)=O)([O-:3])=[O:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[N+:1]([C:4]1[C:13]2[O:12][CH2:11][CH2:10][O:9][C:8]=2[CH:7]=[CH:6][C:5]=1[NH:36][C:39](=[O:24])[O:45][C:41]([CH3:44])([CH3:43])[CH3:42])([O-:3])=[O:2]Participants
5
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 5-nitro-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid (3.80 g, 16.9 mmol), diphenylphosphoryl azide (5.10 g, 18.6 mmol) and triethylamine (1.88 g, 18.6 mmol) in tert-butanol (50 mL) was stirred at 100° C. for 16 h. The reaction mixture was cooled to 20° C., and the solvent removed. The residue was dissolved in DCM (150 mL) and washed with water (150 mL×2), and the solvent was removed. The residue was purified by silica gel column (10% v/v EtOAc in PE) to give tert-butyl 5-nitro-2,3-dihydrobenzo[b][1,4]dioxin-6-ylcarbamate (2.30 g, 46% yield). ESI MS: m/z 297 [M+H]+.
Workup
- temperatureThe reaction mixture was cooled to 20° C.
- customthe solvent removed
- dissolutionThe residue was dissolved in DCM (150 mL)
- washwashed with water (150 mL×2)
- customthe solvent was removed
- customThe residue was purified by silica gel column (10% v/v EtOAc in PE)
Sources & evidence
- ORD record
- ord-bbd58b2b84c0439ab0c3533e7320dec8
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249162B2
Reaction notes
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