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Water → trans-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

HRID 487627
ノート
印刷プレビュー

反応式

HRID 487627 の反応式
[OH:1][C@@H:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:4]=2[C@H:3]1[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])=[CH:18][C:17]1=[O:31].N1C=CC=CC=1.[C:38](OC(=O)C)(=[O:40])[CH3:39].O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:38]([O:1][C@@H:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:4]=2[C@H:3]1[N:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])=[CH:18][C:17]1=[O:31])(=[O:40])[CH3:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131718356trans-3-hydroxy-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 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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

In 15 ml of anhydrous methylene chloride, is dissolved 1.32 g of trans-3-hydroxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-4-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 1. Then, 0.49 ml of pyridine and 73 mg of 4-dimethylaminopyridine are added. Then, 0.43 ml of acetic anhydride is dropped thereinto at 0° C. and reacted at room temperature for 30 minutes. After stopping the reaction by adding water to the reaction mixture, it is extracted with ether. The organic layer is successively washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The inorganic matter is filtered off and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography using 1/3 mixture of ethyl acetate/methylene chloride as a developing solvent to obtain 1.45 g of trans-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.

後処理

  1. customat 0° C. and reacted at room temperature for 30 minutes
  2. customthe reaction
  3. extractionis extracted with ether
  4. washThe organic layer is successively washed with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe inorganic matter is filtered off
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography
  9. addition1/3 mixture of ethyl acetate/methylene chloride as a developing solvent

出典と根拠

ORDレコード
ord-7231cbefef484ca2adcde9aa423ac46a
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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