Diisopropylamine → Methyl 5-bromo-2-methyl-2-phenyl-pentanecarboxylate

HRID 1167096노트

반응식

HRID 1167096 반응식
C([Li])CCC.C(N[CH:10]([CH3:12])[CH3:11])(C)C.C1([CH:19](C)[C:20]([O:22][CH3:23])=[O:21])C=CC=CC=1.[Br:25][CH2:26][CH2:27][CH2:28]Br.[CH3:30][CH2:31][CH2:32][CH2:33][CH2:34]C>O1CCCC1>[Br:25][CH2:26][CH2:27][CH2:28][C:10]([CH3:11])([C:12]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:19][C:20]([O:22][CH3:23])=[O:21]

참가 물질

7

반응물 5

HCID 7912DiisopropylamineHCID 80011,3-DibromopropaneHCID 8058HexaneHCID 569653Methyl alpha-methylbenzeneacetateHCID 178418339Butyllithium

생성물 1

HCID 22995606Methyl 5-bromo-2-methyl-2-phenyl-pentanecarboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-10 °C

실험 절차

15 g (0.234 mol) of n-butyl lithium as a 2.5 molar solution in hexane are added dropwise to a solution of 32.8 ml (0.234 mol) of diisopropylamine in 200 ml of anhydrous tetrahydrofuran at −30° C. and stirred for 10 minutes at −10° C. 38.4 g (0.234 mol) of methyl 2-phenylpropionate are added dropwise at −76° C. and stirred for 30 minutes at this temperature. Then 26.3 ml (0.257 mol) of 1,3-dibromopropane are added, when the addition has ended the cooling bath is removed and the mixture is stirred for 14 hours at ambient temperature. The reaction solution is poured onto 1.2 l of water and extracted with diethylether. The organic phases are extracted with water, dried over sodium sulphate and the solvent is removed. The residue is distilled under high vacuum.

후처리

  1. stirringstirred for 30 minutes at this temperature
  2. additionwhen the addition
  3. customis removed
  4. stirringthe mixture is stirred for 14 hours at ambient temperature
  5. additionThe reaction solution is poured onto 1.2 l of water
  6. extractionextracted with diethylether
  7. extractionThe organic phases are extracted with water
  8. dry with materialdried over sodium sulphate
  9. customthe solvent is removed
  10. distillationThe residue is distilled under high vacuum

출처 및 근거

ORD 기록
ord-17cecb85e5184900a32903ea401b91a3
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617325B1

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