Hydrochloric Acid → Methyl 2-propyl-6-heptenoate

HRID 325813

反応式

HRID 325813 の反応式
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.[C:16]([O:22][CH3:23])(=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20].Br[CH2:25][CH2:26][CH2:27][CH:28]=[CH2:29].Cl>O1CCCC1.C([Li])CCC.CCCCCC.C1(C)C=CC=CC=1>[CH2:18]([CH:17]([CH2:29][CH2:28][CH2:27][CH:26]=[CH2:25])[C:16]([O:22][CH3:23])=[O:21])[CH2:19][CH3:20]

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 12206Methyl valerateHCID 707041-Pentene, 5-bromo-HCID 2724682Lithium diisopropylamide

生成物 1

HCID 20462871Methyl 2-propyl-6-heptenoate収率 43.2%

試薬・触媒・溶媒 4

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒HCID 178418339Butyllithium溶媒

実験手順

To a solution of lithium diisopropyl amide, which was prepared from diisopropylamine (6.6 g) in dry tetrahydrofuran (50 ml) and 15% butyl lithium in hexane solution (38 ml) at -65° to -60° C. in a nitrogen atmosphere, were added dropwise a solution of methyl pentanoate (7 g) in dry tetrahydrofuran (65 ml) followed by a solution of 5-bromo-1-pentene (9 g) in dry tetrahydrofuran (30 ml) at the same temperature. The mixture was stirred for 4 hours at -65° to 0° C. All the operations described above were carried out in a nitrogen atmosphere. Diluted hydrochloric acid (25 ml) and toluene (200 ml) were added at 0° C. to the mixture, which was further stirred. The organic layer was separated, washed with water, dried and concentrated. The resulting oily residue (9 g) was purified by silica gel column chromatography to give colorless oil of methyl 2-propyl-6-heptenoate (4.8 g).

後処理

  1. customThe organic layer was separated
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting oily residue (9 g) was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-03a8983bed7549a7883f36fce2efdad2
出典データセット
uspto-grants-1984_04
特許番号
US04443365

関連ノート

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