Diisopropylamine → Ethyl 2-benzylideneamino-2-ethylhexanoate

HRID 342866

반응식

HRID 342866 반응식
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(NC(C)C)(C)C.[CH:19](=[N:26][CH:27]([CH2:33][CH3:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29])C1C=CC=CC=1.C(I)CCC>C1COCC1.O.C(OCC)C>[CH:19](=[N:26][C:27]([CH2:33][CH3:34])([CH2:1][CH2:2][CH2:3][CH3:4])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:8]1[CH:7]=[CH:6][CH:11]=[CH:10][CH:9]=1

참가 물질

8

반응물 5

HCID 7912DiisopropylamineHCID 8058HexaneHCID 10962Butyl iodideHCID 10331026Ethyl 2-benzylideneaminobutyrateHCID 178418339Butyllithium

생성물 1

HCID 10107458Ethyl 2-benzylideneamino-2-ethylhexanoate수율 100%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 21584184Diethylether water용매

실험 절차

A 1.6M solution of n-butyl lithium in hexane (33 mmoles, Aldrich) was added to a solution of diisopropylamine (40 mmoles) in THF (21 ml) at a temperature of 5°-10° C. When addition was complete, the mixture was added to a solution of the product from step (b) (30 mmoles) in THF (20 ml) at a temperature of 5°-10° C. When addition was complete, n-butyl iodide (40 mmoles) was added and the mixture allowed to warm to room temperature. After 20 hours, the mixture was poured into water/diethyl ether (1.1 L/0.5 L) and the organic layer separated, washed with brine (1.1 L), dried and evaporated in vacuo to give the desired product as an amber liquid (100% yield).

후처리

  1. additionWhen addition
  2. additionWhen addition
  3. customthe organic layer separated
  4. washwashed with brine (1.1 L)
  5. customdried
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-456d6594309a4628989b501e42d82b3f
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859240

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