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Ammonium Chloride → Methyl 4-[(4E)-3-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzoate

HRID 1920579
ノート
印刷プレビュー

反応式

HRID 1920579 の反応式
C([Li])CCC.[Br-].[OH:7][C:8]1[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:34]([O:36][C:37](=[O:59])[CH2:38][C:39]1([CH2:42][CH2:43][CH:44]([CH:57]=O)[CH2:45][CH2:46][C:47]2[CH:56]=[CH:55][C:50]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][CH:48]=2)[CH2:41][CH2:40]1)[CH3:35].[Cl-].[NH4+]>CCCCCC.C1COCC1>[CH2:34]([O:36][C:37](=[O:59])[CH2:38][C:39]1([CH2:42][CH2:43][CH:44](/[CH:57]=[CH:10]/[C:9]2[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=2[OH:7])[CH2:45][CH2:46][C:47]2[CH:56]=[CH:55][C:50]([C:51]([O:53][CH3:54])=[O:52])=[CH:49][CH:48]=2)[CH2:41][CH2:40]1)[CH3:35]
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 25517Ammonium ChlorideHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 57965765Methyl 4-{5-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-3-formylpentyl}benzoateHCID 178418339Butyllithium

生成物 1

HCID 57965770Methyl 4-[(4E)-3-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

At 0° C., 0.6 ml (1.5 mmol) of a 2.5 M solution of n-butyllithium in hexane is slowly added to a solution of 359 mg (0.799 mmol) of (2-hydroxybenzyl)triphenylphosphonium bromide in 5 ml of anhydrous THF, and the mixture is stirred for 45 min. At this temperature, 192 mg (0.53 mmol) of methyl 4-{5-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-3-formylpentyl}benzoate are then added slowly, and the mixture is stirred at 0° C. for 2 hours. After complete conversion, saturated ammonium chloride solution is added to the reaction solution, which is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is evaporated to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1). This gives 178.5 mg (74% of theory) of a colorless oil.

後処理

  1. stirringthe mixture is stirred at 0° C. for 2 hours
  2. concentrationis then concentrated to dryness
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent is evaporated to dryness

出典と根拠

ORDレコード
ord-fbc0edfa9b324e3a85db8cde2ae34538
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08168821B2

反応ノート

読み込み中…

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