Potassium Carbonate → methyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

HRID 877943Notes

Reaction equation

HRID 877943 reaction equation
C([O:4][CH2:5][C@H:6]1[O:11][C:10]([CH3:13])([CH3:12])[O:9][C@@H:8]([CH2:14][C:15]([O:17][CH2:18]C)=[O:16])[CH2:7]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][CH2:5][C@H:6]1[O:11][C:10]([CH3:12])([CH3:13])[O:9][C@@H:8]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 53339171ethyl 2-((4R,6S)-6-(acetoxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Product 1

HCID 10560752methyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

Mixture of ethyl 2-((4R,6S)-6-(acetoxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (80 grams), potassium carbonate (21 grams) in methanol (400 ml) was stirred for 2 hours at 0-10° C. The reaction mixture was quenched with water and then the reaction mixture extracted into methylene chloride and washed it with water. The methylene chloride from the reaction mixture was distilled off under reduced pressure to get the title compound.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionthe reaction mixture extracted into methylene chloride
  3. washwashed it with water
  4. distillationThe methylene chloride from the reaction mixture was distilled off under reduced pressure

Sources & evidence

ORD record
ord-479700964776427eaf2efd9b91fe2042
Source dataset
uspto-grants-2015_03
Patent number
US08987444B2

Reaction notes

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