2-(Triphenylphosphoranylidene)propionaldehyde → (E)-4-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-methylbut-2-enaldehyde

HRID 1781529Notes

Reaction equation

HRID 1781529 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[C:4]=1[CH2:21][CH:22]=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:31]([CH3:34])[CH:32]=[O:33])C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[C:4]=1[CH2:21]/[CH:22]=[C:31](\[CH3:34])/[CH:32]=[O:33]

Participants

4

Reactant 2

HCID 42809872-(Triphenylphosphoranylidene)propionaldehydeHCID 111208852-(1,3-Dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-acetaldehyde

Product 1

HCID 88264149(E)-4-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl-3-oxoisobenzofuran-5-yl)-2-methylbut-2-enaldehyde

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy -7-methyl-3-oxoisobenzofuran-5-yl)acetaldehyde (10.3 g) and 2-(triphenyl-phosphoranylidene)-propionaldehyde (11.6 g) in toluene (250 ml) was refluxed for 7 hours. The solvent was removed under vacuum and the residue was chromatographed on silica gel, eluting with 9:1 hexane:ethyl acetate, to afford (E)-4-(1,3-dihydro-6-methoxy-4-methoxyethoxymethoxy-7-methyl -3-oxoisobenzofuran-5-yl)-2-methylbut-2-enaldehyde, mp 67°-68° C., (methylene chloride/hexane).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was chromatographed on silica gel
  3. washeluting with 9:1 hexane

Sources & evidence

ORD record
ord-4f4f7c5bfbac4cb282ab0edfc243fca8
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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