Triphenylphosphine → 4-Methoxybenzaldehyde

HRID 1451154Notes

Reaction equation

HRID 1451154 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 12127IsovanillinHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 312444-Methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Namely, (R)-(+)-endo-2-norborneol (2) in tetrahydrofuran is reacted under reflux with 3-hydroxy-4-methoxybenzaldehyde in the presence of diethyl azodicarboxlate and triphenyl phosphine to obtain 3-[(2S)-exo-bicyclo[2.2.1]hepto-2-yloxy]-4-methoxybenzaldehyde (6), then via three steps (as shown in EPO 428 313 A), and the pyrimidone derivative (9) is derived.

Sources & evidence

ORD record
ord-225b07b408304336bd47a22d649a6345
Source dataset
uspto-grants-1997_02
Patent number
US05604120

Reaction notes

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