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Formic Acid → 4-[4-(tert-Butoxycarbonyl)phenyl]-2-[4-(methoxycarbonyl)benzyl]butanoic acid

HRID 1913774
ノート
印刷プレビュー

反応式

HRID 1913774 の反応式
C(N(CC)CC)C.C(O)=O.[C:11]([O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=2)(C(OCC=C)=O)[C:27]([O:29]CC=C)=[O:28])=[CH:20][CH:19]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([O:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH:26]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=2)[C:27]([OH:29])=[O:28])=[CH:22][CH:23]=1)=[O:17])([CH3:13])([CH3:14])[CH3:12]
参加物反応条件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 284Formic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 59180509Diallyl {2-[4-(tert-butoxycarbonyl)phenyl]ethyl}[4-(methoxycarbonyl)benzyl]malonate

生成物 1

HCID 591805004-[4-(tert-Butoxycarbonyl)phenyl]-2-[4-(methoxycarbonyl)benzyl]butanoic acid収率 70.2%

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
100 °C

実験手順

A solution of 0.79 ml (5.66 mmol) of triethylamine and 0.16 ml (4.29 mmol) of formic acid in 10 ml of dioxane is added to a solution of 920 mg (1.71 mmol) of diallyl {2-[4-(tert-butoxycarbonyl)phenyl]ethyl}[4-(methoxycarbonyl)benzyl]malonate, 31.5 mg (0.12 mmol) of triphenylphosphine and 7.7 mg (0.03 mmol) of palladium acetate in 10 ml of dioxane at room temperature. The reaction mixture is then stirred at 100° C. for 12 hours. After conversion is complete, the reaction solution is cooled and the solvent is removed in vacuo. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→1:1). 497 mg (1.2 mmol, 61% yield) of a colourless solid are obtained.

後処理

  1. temperaturethe reaction solution is cooled
  2. customthe solvent is removed in vacuo
  3. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→1:1)

出典と根拠

ORDレコード
ord-a52f1a2c8080404ba05a72dfe7f94282
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08609727B2

反応ノート

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