Triphenylphosphine → 3-(Bicyclo[2.2.1]hept-2-yloxy)-4-methoxybenzaldehyde

HRID 893395Notes

Reaction equation

HRID 893395 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.[CH2:12]1[CH:16]2[CH2:17][C@H:18](O)[CH:14]([CH2:15]2)[CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH:14]12[CH2:15][CH:16]([CH2:17][CH2:18]1)[CH2:12][CH:13]2[O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[CH:2]=[O:1]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 12127IsovanillinHCID 5462977Diethyl azodicarboxylateHCID 12313474Bicyclo(2.2.1)heptan-2-ol, exo-

Product 1

HCID 140101523-(Bicyclo[2.2.1]hept-2-yloxy)-4-methoxybenzaldehydeYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a magnetically-stirred solution of isovanillin (10 mmol, 1.52 g) in dry tetrahydrofuran (15 mL) at -10° C. is added endo-norborneol (10 mmol, 1.12 g) followed by triphenylphosphine (14 mmol, 3.67 g). After a few minutes, a solution of diethylazodicarboxylate (14 mmol, 2.44 g; 2.22 mL) in dry tetrahydrofuran (5 mL) is added dropwise at -10° C. and the resulting solution is allowed to warm to room temperature over 20 hours. The solvent is removed in vacuo and the residue partitioned between ethyl acetate and water. The organic phase is dried (Na2SO4) and concentrated in vacuo to afford the crude product. This material is purified by flash chromatography (SiO2 : 20% ethyl acetate/hexane) to give the title compound as a colorless oil (4.07 mmol, 1.00 g; 41%).

Workup

  1. waitAfter a few minutes
  2. customThe solvent is removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. dry with materialThe organic phase is dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product
  7. customThis material is purified by flash chromatography (SiO2 : 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2eceb61db7ea4224961ce5aa9030a811
Source dataset
uspto-grants-1992_06
Patent number
US05124455

Reaction notes

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