Water → HCID 86721445、化合物

HRID 869594ノート

反応式

HRID 869594 の反応式
[O:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[H-].[Na+].Br[CH2:15][C:16]1[CH:35]=[CH:34][C:19]2/[C:20](=[C:30](/[CH3:33])\[C:31]#[N:32])/[C:21]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:22]=3[O:23][CH2:24][C:18]=2[CH:17]=1.O>C1COCC1>[C:31](/[C:30](=[C:20]1/[C:21]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:22]=2[O:23][CH2:24][C:18]2[CH:17]=[C:16]([CH2:15][CH:3]([C:2](=[O:1])[CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:35]=[CH:34][C:19]/1=2)/[CH3:33])#[N:32]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 238498Ethyl 3-oxohexanoateHCID 86721333(E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile

生成物 1

HCID 86721445HCID 86721445、化合物収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

[step 1] Ethyl 3-oxohexanoate (883 mg, 5.58 mmol) was dissolved in THF (9 mL), sodium hydride (60% w/w, 190 mg, 4.75 mmol) was added, and the mixture was stirred at room temperature for 30 min. To the mixture was added dropwise a solution (9 mL) of (E)-2-[8-(bromomethyl)-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (1.0 g, 2.79 mmol) obtained in Reference Example 1 in tetrahydrofuran, and the mixture was stirred at room temperature overnight. Water was added to the mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 v/v) to give (E)-ethyl 2-{[11-(1-cyanoethylidene)-3-fluoro-6,11-dihydrodibenzo[b,e]oxepin-8-yl]methyl}-3-oxohexanoate (1.19 g, 98%).

後処理

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted 3 times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 v/v)

出典と根拠

ORDレコード
ord-30f307f5c15542bfa4c29ec06803e8bc
出典データセット
uspto-grants-2015_03
特許番号
US08969345B2

反応ノート

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