Dihydrocoumarin → Chroman-2-ol
Reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[O:11][C:9](=[O:10])[CH2:8][CH2:7][C:5]=2[CH:6]=1.O>C1(C)C=CC=CC=1>[O:11]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[CH2:7][CH2:8][CH:9]1[OH:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Dihydrocoumarin (5 g, 33.74 mmol) was dissolved in 50 mL of toluene and cooled to −78° C. Dibal (1 M solution in toluene, 38 mL, 38 mmol) was added to the reaction flask over a 45 minutes period. The reaction mixture was stirred at this temperature for 2 h. Water (50 mL) was added slowly along with some toluene to ensure a smooth stirring of the reaction mixture. The slurry was warmed to room temperature and stirring was continued overnight. The organic layer was decanted and dried with magnesium sulfate. Solvent was removed via rotatory evaporator to give compound 5A as a clear oil (4.5 g, 89%). MS: 149 (M−1)+
Workup
- stirringa smooth stirring of the reaction mixture
- temperatureThe slurry was warmed to room temperature
- stirringstirring
- waitwas continued overnight
- customThe organic layer was decanted
- dry with materialdried with magnesium sulfate
- customSolvent was removed via rotatory evaporator
Sources & evidence
- ORD record
- ord-9148c864b2a94da7a668e4220db7afb1
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109222B2
Reaction notes
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