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Hydrochloric Acid → trans-3-acetoxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyran

HRID 487628
ノート
印刷プレビュー

反応式

HRID 487628 の反応式
[C:1]([O:4][C@@H:5]1[C:10]([CH3:12])([CH3:11])[O:9][C:8]2[CH:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:7]=2[C@H:6]1[N:19]1[CH:24]=[CH:23][C:22]([CH2:25][O:26][Si](C(C)(C)C)(C)C)=[CH:21][C:20]1=[O:34])(=[O:3])[CH3:2].Cl>CO.O1CCOCC1>[C:1]([O:4][C@@H:5]1[C:10]([CH3:12])([CH3:11])[O:9][C:8]2[CH:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:7]=2[C@H:6]1[N:19]1[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[CH:21][C:20]1=[O:34])(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 131718355trans-3-acetoxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran

生成物 1

HCID 67821378trans-3-acetoxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyran収率 95.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 31275
1,4-Dioxane
溶媒

実験手順

In 15.0 ml of methanol, is dissolved 1.45 g of trans-3-acetoxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxy-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 4. Then, 3.00 ml of 4N hydrochloric acid in dioxane is added thereto at 0° C. and reacted at room temperature for 2 hours. The reaction mixture is concentrated under reduced pressure, the residue is mixed with water and ethyl acetate, and the product is extracted by ethyl acetate. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then, the inorganic matter is filtered off and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography using ethyl acetate as a developing solvent to obtain 1.06 g of trans-3-acetoxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-hydroxymethyl-1-pyridinyl)-2H-benzo[b]pyran.

後処理

  1. customat 0° C. and reacted at room temperature for 2 hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additionthe residue is mixed with water and ethyl acetate
  4. extractionthe product is extracted by ethyl acetate
  5. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThen, the inorganic matter is filtered off
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customThe residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-a89a39ed35484a80bb1e92a62f3e07b5
出典データセット
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05296492

反応ノート

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