Potassium Carbonate → tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

HRID 993417ノート

反応式

HRID 993417 の反応式
[CH3:1][C:2]1([CH3:21])[O:7][C@@H:6]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][C@@H:4]([CH2:16][O:17]C(C)=O)[O:3]1.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:17][CH2:16][C@H:4]1[O:3][C:2]([CH3:1])([CH3:21])[O:7][C@@H:6]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5]1

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 9839384(4R-cis)-6-[(Acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester

生成物 1

HCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

In 100 mL of methanol was dissolved 10 g (33.1 mmol) of tert-butyl 2-{(4R,6S)-2,2-dimethyl-6-[(methylcarbonyloxy)methyl]-1,3-dioxan-4-yl}acetate [synthesized by the process described in Example 8], and under ice-cooling and stirring, 0.46 g (3.3 mmol) of potassium carbonate was added. The mixture was further stirred under ice-cooling for 4 hours. From this reaction mixture, the reaction solvent was distilled off by heating under reduced pressure, and the residue was diluted with 50 mL of water and neutralized with 0.1 N-hydrochloric acid. This solution was extracted with ethyl acetate and the resulting organic layer was washed with water and dehydrated over anhydrous sodium sulfate. The solvent was then distilled off by heating under reduced pressure. The oily residue was decompressed to 1 Torr or less with a vacuum pump to remove the solvent almost thoroughly. As a result, 8.6 g of tert-butyl 2-[(4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate (colorless oil) was obtained in a yield of 100%.

後処理

  1. customsynthesized by the process
  2. temperaturecooling
  3. stirringThe mixture was further stirred under ice-
  4. temperaturecooling for 4 hours
  5. distillationFrom this reaction mixture, the reaction solvent was distilled off
  6. temperatureby heating under reduced pressure
  7. additionthe residue was diluted with 50 mL of water and neutralized with 0.1 N-hydrochloric acid
  8. extractionThis solution was extracted with ethyl acetate
  9. washthe resulting organic layer was washed with water
  10. distillationThe solvent was then distilled off
  11. temperatureby heating under reduced pressure
  12. customto remove the solvent almost thoroughly

出典と根拠

ORDレコード
ord-a2f0c28042c042ebb41a382032e6c7a6
出典データセット
uspto-grants-2002_10
特許番号
US06472544B1

反応ノート

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