Hydrochloric Acid → 4-[3-Chloro-4-(1-methyl-2-oxo-ethyl)-phenoxy]-benzonitrile

HRID 1095900

反応式

HRID 1095900 の反応式
CC(C)([O-])C.[K+].[C:7]([C:10]1[CH:24]=[CH:23][C:13]([O:14][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)=[CH:12][C:11]=1[Cl:25])(=O)[CH3:8].[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.[C:50]([O-:53])(O)=O.[Na+]>C1COCC1>[Cl:25][C:11]1[CH:12]=[C:13]([CH:23]=[CH:24][C:10]=1[CH:7]([CH3:8])[CH:50]=[O:53])[O:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 643355014-(4-Acetyl-3-chlorophenoxy)benzonitrile

生成物 1

HCID 866459484-[3-Chloro-4-(1-methyl-2-oxo-ethyl)-phenoxy]-benzonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Potassium tert-butoxide (248 mg) was added to a solution 4-(4-acetyl-3-chloro-phenoxy)-benzonitrile (500 mg) and (methoxymethyl)-triphenylphosphonium chloride (694 mg) in THF (10 ml) at room temperature. The mixture was stirred for 1 h at room temperature. 25% aqueous HCl (4 ml) was added. The resulting mixture was stirred 1 h at room temperature and poured then carefully to a saturated aqueous NaHCO3 solution. After neutralization, the mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (450 mg) as yellow oil. MS (m/e, ISP neg. ion)=284.3 [M−H+].

後処理

  1. stirringThe resulting mixture was stirred 1 h at room temperature
  2. additionpoured
  3. extractionAfter neutralization, the mixture was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated to an oil
  6. customThe residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2)

出典と根拠

ORDレコード
ord-e8ddd91e87ed4d8bb16d6688a903ae58
出典データセット
uspto-grants-2012_03
特許番号
US08138189B2

関連ノート

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