Methanol → HCID 15062404, compound

HRID 486849Notes

Reaction equation

HRID 486849 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 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 940 mg (4.26 mmol) of (-)-2,2-dimethyl-6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-one (98% ee), 882 mg (6.39 mmol) of potassium carbonate and 10 ml of methanol was stirred at room temperature for 12 hours. After completion of the reaction, methanol was distilled off, and the resultant residue was neutralized with 10% HCl and then extracted with ethyl acetate, followed by drying 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 510 mg (yield 74%) of (-)-6-chloromethyltetrahydropyran-2,4-dione.

Workup

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

Sources & evidence

ORD record
ord-118aa606c6fb42efbeefd59031e5a285
Source dataset
uspto-grants-1994_03
Patent number
US05292891

Reaction notes

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