Benzyl Alcohol → HCID 19066311, compound
Reaction equation
[O:1]1[CH:6]=[CH:5][C:4](C(O)=O)=[CH:3][CH2:2]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:17])C=CC=CC=1.C([N:29]([CH2:32]C)CC)C.[CH2:34]([OH:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCOCC1>[CH2:34]([O:41][C:32]([NH:29][C:4]1[CH:5]=[CH:6][O:1][CH2:2][CH:3]=1)=[O:17])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 4-pyranylcarboxylic acid (2.28 gm, 20 mmol), diphenylphosphorylazide (4.31 ml, 20 mmol), triethylamine (2.78 ml, 20 mmol) in dioxane (40 ml) was heated in a 100° C. oil bath under dry nitrogen for 1 hour. Benzyl alcohol (2.7 ml, 26 mmol) was added, and heating was continued at 100° C. for 22 hours. The mixture was cooled, filtered from a white precipitate and concentrated. The residue was dissolved in 2N HCl and extracted twice with EtOAc. The extracts were washed with water, sodium bicarbonate, brine and then dried over MgSO4, and concentrated to an oil which solidified upon standing. The oil was chromatographed (30% to 60% EtOAc/Hex) to give 1.85 g of a white solid (40%).
Workup
- temperatureheating
- temperatureThe mixture was cooled
- filtrationfiltered from a white precipitate
- concentrationconcentrated
- dissolutionThe residue was dissolved in 2N HCl
- extractionextracted twice with EtOAc
- washThe extracts were washed with water, sodium bicarbonate, brine
- dry with materialdried over MgSO4
- concentrationconcentrated to an oil which
- customThe oil was chromatographed (30% to 60% EtOAc/Hex)
Sources & evidence
- ORD record
- ord-0a409046cc1544729b8c431d33de87e7
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05789416
Reaction notes
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