Hydrochloric Acid → Methyl 2-propyl-6-heptenoate

HRID 325813

반응식

HRID 325813 반응식
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]

참가 물질

10

반응물 5

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

생성물 1

HCID 20462871Methyl 2-propyl-6-heptenoate수율 43.2%

시약·촉매·용매 4

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매HCID 178418339Butyllithium용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-03a8983bed7549a7883f36fce2efdad2
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04443365

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