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Ethyl Acetate → HCID 90029693, 화합물

HRID 2200128
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HRID 2200128 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Br:17])[CH:8]=1.[N+](C1C=C[C:24]([C:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH:28]=2)=C(C(F)(F)F)C=1)([O-])=O.CC[O:46]C(C)=O>C1COCC1>[C:36]([O:35][C:33]([N:30]1[CH2:31][CH2:32][CH:27]([C:24](=[O:46])[C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Br:17])[CH:8]=2)[CH2:28][CH2:29]1)=[O:34])([CH3:39])([CH3:38])[CH3:37]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

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HCID 8857Ethyl AcetateHCID 20634891,3-Dibromo-5-(trifluoromethyl)benzeneHCID 66711203HCID 66711203, 화합물HCID 178418339Butyllithium

생성물 1

HCID 90029693HCID 90029693, 화합물수율 27%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

반응 조건

온도
-78 °C

실험 절차

Add n-butyllithium (2.5 N, 1.44 mL) to the solution of 1,3-dibromo-5-(trifluoromethyl)benzene (1 g, 3.28 mmol) in THF (15 mL) at −78° C. and stir the mixture at −78° C. for 1 hr. Then add tert-butyl 4-(methoxy(methyl)carbamoyl) piperidine-1-carboxylate (1.4 g, 4.92 mmol) obtained in Step 1 to the mixture and continue stirring. TLC (PE:EtOAc=5:1) shows the reaction is complete. Quench the reaction mixture with saturated ammonium chloride solution. Partition between EtOAc and water, separate the organic layer, and wash with brine, dry over anhydrous sodium sulfate, concentrate to give the crude product. Purify by flash chromatography (silica gel, DCM:MeOH=20:1) to afford the product (387 mg, 27%). MS: (M+1): 436.

후처리

  1. customQuench the reaction mixture with saturated ammonium chloride solution
  2. customPartition between EtOAc and water
  3. customseparate the organic layer
  4. washwash with brine
  5. dry with materialdry over anhydrous sodium sulfate
  6. concentrationconcentrate
  7. customto give the crude product
  8. customPurify by flash chromatography (silica gel, DCM:MeOH=20:1)

출처 및 근거

ORD 기록
ord-b28f36bf2bec47a2b8a0f8b097babc33
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09359338B2

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