Thionyl Chloride → 3-methyl-4-chloro-3,4-dihydro-2H-pyran-2-methanol acetate

HRID 27645Notes

Reaction equation

HRID 27645 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

HCID 24386Thionyl ChlorideHCID 129405143-methyl-6-ethoxy-3,6-dihydro-2H-pyran-2-methanol acetate

Product 1

HCID 129405153-methyl-4-chloro-3,4-dihydro-2H-pyran-2-methanol acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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

  1. concentrationconcentrated
  2. customto give 0.098 g

Sources & evidence

ORD record
ord-2465ff2a7d9b47648226210c24f454c9
Source dataset
uspto-grants-1980_09
Patent number
US04222943

Reaction notes

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