1-Iodonaphthalene → Methyl 4-(1-naphthyl)-2-oxobutyrate

HRID 278471

反応式

HRID 278471 の反応式
P(CCCC)(CCCC)CCCC.CCN(CC)CC.[OH:21][CH:22]([CH:27]=[CH2:28])[C:23]([O:25][CH3:26])=[O:24].I[C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].O>[C:38]1([CH2:28][CH2:27][C:22](=[O:21])[C:23]([O:25][CH3:26])=[O:24])[C:39]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:35]=[CH:36][CH:37]=1

参加物

8

反応物 4

HCID 70041-IodonaphthaleneHCID 8471TriethylamineHCID 13831TributylphosphineHCID 545123Methyl 2-hydroxybut-3-enoate

生成物 1

HCID 18370780Methyl 4-(1-naphthyl)-2-oxobutyrate収率 6.9%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of Pd(OAc)2 (340 mg), nBu3P (613 mg), and Et3N (1.99 g) in DMF (30 ml) was added methyl 2-hydroxy-3-butenoate (1.76 g) followed by 1-iodonaphthalene (5.0 g), and the reaction mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was poured into water (300 ml) and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel (130 g) column chromatography eluting with hexane/ethyl acetate (50:1) to give methyl 4-(1-naphthyl)-2-oxobutyrate (254 mg) as a red oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel (130 g) column chromatography
  6. washeluting with hexane/ethyl acetate (50:1)

出典と根拠

ORDレコード
ord-9e3c425c714a4a85a45538e47de2e0fe
出典データセット
uspto-grants-2002_03
特許番号
US06359145B1

関連ノート

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