Diisopropylamine → 5-Hexenoic acid, 2-[(phenylmethylene)amino]-, methyl ester

HRID 22530

반응식

HRID 22530 반응식
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[CH3:13][O:14][C:15](=[O:25])[CH2:16][N:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.BrCCC=C.CN(C)P(N(C)C)(N(C)C)=O>O1CCCC1.CCCCCC.O>[CH3:13][O:14][C:15](=[O:25])[CH:16]([CH2:11][CH2:10][CH:9]=[CH2:8])[N:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

9

반응물 5

HCID 7912DiisopropylamineHCID 12679HexamethylphosphoramideHCID 21241Homoallyl bromideHCID 4169153Methyl [(phenylmethylidene)amino]acetateHCID 178418339Butyllithium

생성물 1

HCID 120394615-Hexenoic acid, 2-[(phenylmethylene)amino]-, methyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

Dissolve diisopropylamine (15.4 mL, 110 mmol) in tetrahydrofuran (250 mL), place under a nitrogen atmosphere and cool to -78° C. Add n-butyllithium (39 mL of a 2.7M solution in hexane, 105 mmol). Stir for 30 minutes and add, by dropwise addition, a solution of N-(phenylmethylene)glycine methyl ester (17.7 g, 100 mmol) in tetrahydrofuran (25 mL). Stir for 15 minutes and add 4-bromobutene (13.5 g, 100 mmol) and allow to warm slowly to room temperature. Add hexamethylphosphoramide (20 mL, 100 mmol) and stir under a nitrogen atmosphere for 3 hours. Pour into water, extract into ethyl ether and wash with brine several times. Dry (MgSO4) and evaporate the solvent in vacuo to give the title compound as an amber oil (25 g).

후처리

  1. additionadd, by dropwise addition
  2. stirringStir for 15 minutes
  3. temperatureto warm slowly to room temperature
  4. extractionextract into ethyl ether
  5. washwash with brine several times
  6. dry with materialDry (MgSO4)
  7. customevaporate the solvent in vacuo

출처 및 근거

ORD 기록
ord-500cbad420cc42019c59dc884561197b
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428158

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