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Triphenylphosphine → 4-Methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]benzaldehyde

HRID 1826090
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HRID 1826090 반응식
N(C(OCC)=O)=NC(OCC)=O.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=1.[O:26]=[CH:27][C:28]1[CH:36]=[CH:35][C:32]([O:33][CH3:34])=[C:30](O)[CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:34][O:33][C:32]1[CH:35]=[CH:36][C:28]([CH:27]=[O:26])=[CH:29][C:30]=1[O:23][CH2:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([F:24])([F:25])[F:13])=[CH:20][CH:19]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 12127IsovanillinHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 112755102-(4-(Trifluoromethyl)phenyl)ethan-1-ol

생성물 1

HCID 118094914-Methoxy-3-[2-[4-(trifluoromethyl)phenyl]ethoxy]benzaldehyde수율 72.3%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

Under an argon atmosphere, stirring and cooling with ice, diethyl azodicarboxylate (40% toluene solution, 3.80 mL, 8.38 mmol) was added dropwise to a solution of 2-[4-(tri-fluoromethyl)phenyl]ethanol (1.59 g, 8.36 mmol), isovanillin (1.28 g, 8.41 mmol) and triphenylphosphine (2.20 g, 8.39 mmol) in anhydrous tetrahydrofuran (50 mL). After completion of the dropwise addition, the mixture was stirred for 1 hour under cooling with ice, and then allowed to stand overnight at room temperature. The reaction mixture was concentrated and the residue was purified by silica gel column chro-matography (eluent: n-hexane:ethyl acetate=6:1 v/v) to afford 1.96 g (72%) of the title compound as colorless crystals.

후처리

  1. additionAfter completion of the dropwise addition
  2. stirringthe mixture was stirred for 1 hour
  3. temperatureunder cooling with ice
  4. concentrationThe reaction mixture was concentrated
  5. customthe residue was purified by silica gel column chro-matography (eluent: n-hexane:ethyl acetate=6:1 v/v)

출처 및 근거

ORD 기록
ord-dfee7d1c0db24aa68d2005667405d409
출처 데이터셋
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07049342B2

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