Ethyl Acetate → methyl 5-formyl-(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-pentanecarboxylate

HRID 1681971

反応式

HRID 1681971 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:14][CH2:15][CH:16]=C)[CH2:9][C:10](OC)=O.[O:18]=[O+][O-].[H][H].[C:23]([O:26][CH2:27]C)(=[O:25])C>>[CH:16]([CH2:15][CH2:14][C@@H:8]([O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:9][CH2:10][C:23]([O:26][CH3:27])=[O:25])=[O:18]

参加物

5

反応物 4

HCID 8857Ethyl AcetateHCID 24823OzoneHCID 86743990methyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6-heptenoateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 86743989methyl 5-formyl-(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-pentanecarboxylate

実験手順

A solution of 2.56 g of methyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6-heptenoate in 40 ml of ethyl acetate was treated with ozone at -75° C. After completion of the reaction 0.1 g of Pd-on-carbon was added thereto and the mixture was hydrogenated at room temperature. After the hydrogen uptake was finished the catalyst was filtered off and washed with ethyl acetate and the filtrate and washings were evaporated in vacuo There was obtained methyl 5-formyl-(R)-3-[(tetrahydro-2H-pyran-2- yl)oxy]-pentanecarboxylate.

後処理

  1. additionwas added
  2. customwas hydrogenated at room temperature
  3. filtrationwas filtered off
  4. washwashed with ethyl acetate
  5. customthe filtrate and washings were evaporated in vacuo

出典と根拠

ORDレコード
ord-d3eeb5bb118342bba91d9bd58bf0ef56
出典データセット
uspto-grants-1992_12
特許番号
US05175186

関連ノート

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