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

HRID 1826090Notes

Reaction equation

HRID 1826090 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-dfee7d1c0db24aa68d2005667405d409
Source dataset
uspto-grants-2006_05
Patent number
US07049342B2

Reaction notes

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