Reaction equation
[Cl:1][CH:2]([O:4][C:5](Cl)=[O:6])[CH3:3].[CH3:8][C:9]1([CH3:19])[CH2:13][C:12]2[CH:14]=[CH:15][CH:16]=[C:17]([OH:18])[C:11]=2[O:10]1.N1C=CC=CC=1>ClCCl>[C:5](=[O:6])([O:18][C:17]1[C:11]2[O:10][C:9]([CH3:19])([CH3:8])[CH2:13][C:12]=2[CH:14]=[CH:15][CH:16]=1)[O:4][CH:2]([Cl:1])[CH3:3]Participants
5
Conditions
- Temperature
- 20 °C
Procedure
21.5 g (0.15 mole) of 1-chloroethylchloroformate are added in a single portion to a solution of 2,3-dihydro-2,2-dimethyl-7-benzofuranol (24.6 g; 0.15 mole) in dichloromethane (150 ml). The mixture is cooled to between 0° and 5° C., and 12 g (0.15 mole) of pyridine are added dropwise. The mixture is stirred for 3 hours at 20° C. The organic phase is then washed with 2×50 ml of iced water. It is dried over magnesium sulphate and the solvent is evaporated. A yellow oil is obtained which is distilled. 34.1 g of the expected carbonate is then recovered (84% yield).
Workup
- temperatureThe mixture is cooled to between 0° and 5° C.
- washThe organic phase is then washed with 2×50 ml of iced water
- dry with materialIt is dried over magnesium sulphate
- customthe solvent is evaporated
- customA yellow oil is obtained which
- distillationis distilled
- custom34.1 g of the expected carbonate is then recovered (84% yield)
Sources & evidence
- ORD record
- ord-3c480d95de8546edb218b0eba0488c82
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04725680
Linked notes
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