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Hydrochloric Acid → 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1,3-dihydroxypropyl)-1-pyridinyl}-2H-benzo[b]pyran

HRID 487647
ノート
印刷プレビュー

反応式

HRID 487647 の反応式
[C:1]([C:3]1[CH:29]=[CH:28][C:6]2[O:7][C:8]([CH3:27])([CH3:26])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH:17]([OH:24])[CH2:18][C:19](OCC)=[O:20])=[CH:13][C:12]3=[O:25])[C:5]=2[CH:4]=1)#[N:2].[BH4-].[Na+].Cl>O1CCOCC1>[C:1]([C:3]1[CH:29]=[CH:28][C:6]2[O:7][C:8]([CH3:26])([CH3:27])[CH:9]=[C:10]([N:11]3[CH:16]=[CH:15][C:14]([CH:17]([OH:24])[CH2:18][CH2:19][OH:20])=[CH:13][C:12]3=[O:25])[C:5]=2[CH:4]=1)#[N: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 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 190925286-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1-hydroxy-2-ethoxycarbonylethyl)-1-pyridinyl}-2H-benzo[b]pyran

生成物 1

HCID 190925486-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1,3-dihydroxypropyl)-1-pyridinyl}-2H-benzo[b]pyran収率 67.1%

試薬・触媒・溶媒 1

HCID 31275
1,4-Dioxane
溶媒

実験手順

In 50 ml of dioxane, is dissolved 3.87 g of 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1-hydroxy-2-ethoxycarbonylethyl)-1-pyridinyl}-2H-benzo[b]pyran obtained in Example 31. Then, 50 ml of an aqueous solution containing 3.71 g of sodium borohydride is added at room temperature and reacted at room temperature for one hour. After stopping the reaction by adding 100 ml of 2M aqueous hydrochloric acid, the reaction mixture is extracted with ethyl acetate. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium 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 1/10 mixture of methanol/methylene chloride as a developing solvent. Thus, 2.32 g of 6-cyano-2,2-dimethyl-4-{1,2-dihydro-2-oxo-4-(1,3-dihydroxypropyl)-1-pyridinyl}-2H-benzo[b]pyran is obtained.

後処理

  1. additionis added at room temperature
  2. customreacted at room temperature for one hour
  3. customthe reaction
  4. extractionthe reaction mixture is extracted with ethyl acetate
  5. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe inorganic matter is filtered off
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customThe residue is purified by silica gel column chromatography
  10. addition1/10 mixture of methanol/methylene chloride as a developing solvent

出典と根拠

ORDレコード
ord-377c586b1fa0422ea810e99baf9b20ba
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

読み込み中…

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