Benzyl Alcohol → Benzyl cyclopent-3-en-1-ylcarbamate
Reaction equation
C1([C:6]([OH:8])=O)CC=CC1.C1C=CC(P([N:23]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[C:26]1([CH2:32][OH:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:34]1([CH3:40])[CH:39]=[CH:38][CH:37]=CC=1>>[CH:34]1([NH:23][C:6](=[O:8])[O:33][CH2:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:39][CH:38]=[CH:37][CH2:40]1Participants
5
Conditions
- Temperature
- 90 °C
Procedure
To a cooled solution of cyclopent-3-ene-1-carboxylic acid (2.0 g, 17.8 mmol) and DPPA (6.05 g, 22.0 mmol) in toluene (50 mL) was added TEA (2.0 g, 22.0 mmol) dropwise at 0° C. The resulting mixture was then warmed and heated at 90° C. for 1 hour. After being added phenylmethanol (4.0 g, 40 mmol), the mixture was heated at 90° C. for additional 4 hours and then concentrated in vacuo. The residue was purified by silica-gel chromatography to afford benzyl cyclopent-3-en-1-ylcarbamate as a white solid (1.9 g).
Workup
- temperatureThe resulting mixture was then warmed
- temperaturethe mixture was heated at 90° C. for additional 4 hours
- concentrationconcentrated in vacuo
- customThe residue was purified by silica-gel chromatography
Sources & evidence
- ORD record
- ord-c1b241a8b3994f3095824fe1ddcf3d0c
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206191B2
Reaction notes
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