Thionyl Chloride → 3-methyl-4-chloro-3,4-dihydro-2H-pyran-2-methanol acetate
Reaction equation
[C:1]([O:4][CH2:5][CH:6]1[CH:11]([CH3:12])[CH:10]=[CH:9][CH:8](OCC)[O:7]1)(=[O:3])[CH3:2].S(Cl)([Cl:18])=O>CCOCC>[C:1]([O:4][CH2:5][CH:6]1[CH:11]([CH3:12])[CH:10]([Cl:18])[CH:9]=[CH:8][O:7]1)(=[O:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 0.113 g. (0.53 mmol) of 3-methyl-6-ethoxy-3,6-dihydro-2H-pyran-2-methanol acetate in 2 ml. of ether at 0° was added 0.12 g. (1.0 mmol) of thionyl chloride. The mixture was stirred at 0° for 1 hour, at room temperature for 4.75 hours and concentrated to give 0.098 g. (103%) of the crude chloroenol-ether as a colorless oil (ca. 70% pure by nmr).
Workup
- concentrationconcentrated
- customto give 0.098 g
Sources & evidence
- ORD record
- ord-014007f32fa24b6389caf92ae01ef6d7
- Source dataset
- uspto-grants-1981_09
- Patent number
- US04288614
Reaction notes
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