Triphenylphosphine → 4-Methoxy-3-(3-methoxypropoxy)benzaldehyde

HRID 2354968Notes

Reaction equation

HRID 2354968 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[CH3:12][O:13][CH2:14][CH2:15][CH2:16]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH2:16][CH2:15][CH2:14][O:13][CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 12127IsovanillinHCID 741163-Methoxy-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 112183584-Methoxy-3-(3-methoxypropoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hydroxy-4-methoxy-benzaldehyde (3.04 g, 20 mmol) and 3-methoxy-propanol (1.80 g, 20 mmol) in THF (150 mL) is added triphenylphosphine (5.24 g, 20 mmol) at room temperature under nitrogen atmosphere. To the stirring mixture is added diethyl azodicarboxylate (3.11 mL, 20 mmol) over 10 min at room temperature, and the resulting solution is further stirred over 20 h. THF is removed under reduced pressure and the remaining residue is purified by flash chromatography on silica gel (hexane/EtOAc 2/1) to afford the title compound: TLC, Rf (hexane/EtOAc 2/1)=0.2.

Workup

  1. customTHF is removed under reduced pressure
  2. customthe remaining residue is purified by flash chromatography on silica gel (hexane/EtOAc 2/1)

Sources & evidence

ORD record
ord-0b86a26cb15f436e9097c388810a5cee
Source dataset
uspto-grants-2010_07
Patent number
US07754727B2

Reaction notes

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