Methanol → HCID 15062404, compound

HRID 486850Notes

Reaction equation

HRID 486850 reaction equation
CC1(C)O[C:6](=[O:8])[CH:5]=[C:4]([CH2:9][CH:10]([OH:13])[CH2:11][Cl:12])[O:3]1.C(=O)([O-])[O-].[K+].[K+].CO>C(OCC)(=O)C>[Cl:12][CH2:11][CH:10]1[O:13][C:6](=[O:8])[CH2:5][C:4](=[O:3])[CH2:9]1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 11430Potassium CarbonateHCID 14944829HCID 14944829, compound

Product 1

HCID 15062404HCID 15062404, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 470 mg (2.13 mmol) of (+)-2,2-dimethyl-6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-one (99% ee), 441 mg (3.20 mmol) of potassium carbonate and 5 ml of methanol was stirred at room temperature for 9 hours. After completion of the reaction, methanol was distilled off, and the resultant residue was neutralized with 10% HCl, extracted with ethyl acetate, and then dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was subjected to column chromatography (an eluent of hexane:ethyl acetate=3:1), thereby obtaining 270 mg (yield 79%) of (+)-6-chloromethyltetrahydropyran-2,4-dione.

Workup

  1. distillationwas distilled off
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-67274e346de94d29bdce5dc59ad1058c
Source dataset
uspto-grants-1994_03
Patent number
US05292891

Reaction notes

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