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5-Formyl-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamide → Ethyl 2-methoxy-3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]acrylate

HRID 1634516
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인쇄 미리보기

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HRID 1634516 반응식
C(OP([CH:9]([O:15][CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.CC(C)([O-])C.[K+].[F:23][C:24]([F:46])([F:45])[C:25]1[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:33](=[O:44])[C:34]2[CH:39]=[C:38]([CH:40]=O)[CH:37]=[CH:36][C:35]=2[O:42][CH3:43])=[CH:27][CH:26]=1>O1CCCC1>[CH3:16][O:15][C:9](=[CH:40][C:38]1[CH:37]=[CH:36][C:35]([O:42][CH3:43])=[C:34]([C:33](=[O:44])[NH:32][CH2:31][C:28]2[CH:29]=[CH:30][C:25]([C:24]([F:23])([F:45])[F:46])=[CH:26][CH:27]=2)[CH:39]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 120946615-Formyl-2-methoxy-N-[[4-(trifluoromethyl)phenyl]methyl]-benzamideHCID 15638229Ethyl 2-(diethoxyphosphoryl)-2-methoxyacetateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 69758375Ethyl 2-methoxy-3-[4-methoxy-3-[N-[[4-(trifluoromethyl)phenyl]methyl]carbamoyl]phenyl]acrylate수율 78%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

Ethyl 2-(diethoxyphosphoryl)-2-methoxyacetate (265 mg, 1.10 mmol) was dissolved in 3 ml of dehydrated tetrahydrofuran and potassium t-butoxide (123 mg, 1.10 mmol) was added under stirring and cooling with ice under an atmosphere of argon, which was stirred for 30 minutes. Next, N-[[4-(trifluoromethyl)phenyl]methyl]-5-formyl-2-methoxybenzamide (338 mg, 1.00 mmol) dissolved in 2 ml of dehydrated tetrahydrofuran was added. After stirring for 1 hour at room temperature, the reaction mixture was poured into ice water, which was extracted with ethyl acetate, washed with water and brine in sequence, then dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=3:1 v/v) to obtain 330 mg (78%) of the title compound (mixture of geometrical isomers relevant to double bond) as colorless crystals.

후처리

  1. temperaturecooling with ice under an atmosphere of argon
  2. stirringwhich was stirred for 30 minutes
  3. additionwas added
  4. stirringAfter stirring for 1 hour at room temperature
  5. extractionwas extracted with ethyl acetate
  6. washwashed with water and brine in sequence
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography (eluate n-hexane:ethyl acetate=3:1 v/v)

출처 및 근거

ORD 기록
ord-8c95901993cd43b3a668054fa84c23d8
출처 데이터셋
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06506797B1

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