beta-Bromostyrene → 1-Methyl-2-styryl-2-hydroxy-6-piperidone

HRID 259389

반응식

HRID 259389 반응식
[Mg].Br[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:11][N:12]1[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]1=[O:19].[NH4+].[Cl-]>C1COCC1>[CH3:11][N:12]1[C:13](=[O:19])[CH2:14][CH2:15][CH2:16][C:17]1([CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:18]

참가 물질

6

반응물 4

HCID 7667beta-BromostyreneHCID 25517Ammonium ChlorideHCID 1614762,6-Piperidinedione, 1-methyl-HCID 5462224Magnesium

생성물 1

HCID 537761611-Methyl-2-styryl-2-hydroxy-6-piperidone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The Grignard reagent prepared in 300 ml of THF from 24 g (1.0 mole) of magnesium and 42 g (0.30 mole) of β-bromostyrene is decanted from excess metal and added dropwise under nitrogen to a solution of 27 g (0.21 moles) of N-methyl glutarimide at 3°- 5°. After 11/2 hrs. at room temperature, the mixture is treated with 250 ml of saturated NH4Cl solution with cooling. The separated aqueous layer is reextracted and the combined THF extracts washed with salt, dried over MgSO4 and freed of solvent. Product is extracted into hot ether and crystallized on cooling to yield white crystals, mp 108°- 112° C.

후처리

  1. customis decanted from excess metal
  2. custom2 hrs
  3. temperaturewith cooling
  4. washthe combined THF extracts washed with salt
  5. dry with materialdried over MgSO4
  6. extractionProduct is extracted into hot ether
  7. customcrystallized
  8. temperatureon cooling
  9. customto yield white crystals, mp 108°- 112° C.

출처 및 근거

ORD 기록
ord-ecfd5e6d54e74309bff4d1113272e89d
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04038273

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