Diisopropylamine → Methyl 2-methoxy-3-hydroxy-3-(2-dodecylphenyl)propionate

HRID 2165494ノート

反応式

HRID 2165494 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].[CH2:20]([C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH:34]=[O:35])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O1CCCC1>[CH3:13][O:14][CH:15]([CH:34]([OH:35])[C:33]1[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:16]([O:18][CH3:19])=[O:17]

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 80507Methyl methoxyacetateHCID 140975722-DodecylbenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 15617501Methyl 2-methoxy-3-hydroxy-3-(2-dodecylphenyl)propionate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a solution of di-i-propylamine (0.77 ml, 5 mmoles) in tetrahydrofuran (10 ml) at -78° C. was added n-butyl lithium (2.1 ml, 5.5 mmoles) under argon atmosphere. After 15 minutes, methyl methoxyacetate (0.52 g, 5 mmoles) in tetrahydrofuran (2 ml) was added dropwise, with stirring. The resulting enolate solution was stirred at -78° C. for 45 minutes. A solution of 2-dodecylbenzaldehyde (1.65 g, 6 mmoles) in tetrahydrofuran (2 ml) was added. The resulting light-blue mixture became a suspension after 1.5 hours. The reaction mixture was quenched with saturated ammonium chloride solution, diluted with ether and ice-water. The aqueous phase was extracted with ether. The combined organic extract was washed with saturated sodium chloride solution, dried over magnesium sulfate, and evaporated to give the product, which was purified by flash column chromatography (silica, 15% ethyl acetate/hexane). The fractions were pooled to give 620 mg (33%).

後処理

  1. customafter 1.5 hours
  2. customThe reaction mixture was quenched with saturated ammonium chloride solution
  3. additiondiluted with ether and ice-water
  4. extractionThe aqueous phase was extracted with ether
  5. extractionThe combined organic extract
  6. washwas washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto give the product, which
  10. customwas purified by flash column chromatography (silica, 15% ethyl acetate/hexane)
  11. customto give 620 mg (33%)

出典と根拠

ORDレコード
ord-7244ee005ae9490bbdfc9fb4994dceb3
出典データセット
uspto-grants-1990_07
特許番号
US04939279

反応ノート

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