Toluene → 2-Ethyl-4-[6-ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-but-2-enal

HRID 910546Notes

Reaction equation

HRID 910546 reaction equation
[CH2:1]([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][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:4]=1CC=O)[CH3:2].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=C(CC)C=[O:33])C=CC=CC=1.[C:48]1([CH3:54])[CH:53]=[CH:52]C=[CH:50][CH:49]=1>>[CH2:49]([C:48](=[CH:53][CH2:52][C:4]1[C:5]([O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:20])[CH3:19])=[C:6]2[C:10](=[C:11]([CH3:12])[C:3]=1[CH2:1][CH3:2])[CH2:9][O:8][C:7]2=[O:13])[CH:54]=[O:33])[CH3:50]

Participants

4

Reactant 3

HCID 1140TolueneHCID 45855922-(Triphenylphosphoranylidene)butyraldehydeHCID 59794521[6-Ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro isobenzofuran-5-yl]-acetaldehyde

Product 1

HCID 765410332-Ethyl-4-[6-ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-but-2-enalYield 48%

Procedure

[6-Ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-acetaldehyde (90 mg, 0.269 mmol) and 2-(triphenyl-phosphorylidene)-butyraldehyde (98.4 mg, 0.296 mmol) in toluene (3 mL) were heated at 100° C. After 15 hours, a second portion of 2-(triphenyl-phosphanylidene)-butyraldehyde (98.4 mg, 0.296 mmol) was added and the reaction mixture was heated for additional 33 hours. After concentration, the residue was purified by silica gel chromatography to provide 50.3 mg (48%) of the desired product as a pale yellow oil.

Workup

  1. temperaturethe reaction mixture was heated for additional 33 hours
  2. concentrationAfter concentration
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0d83952c75434ed0a213276f35b48181
Source dataset
uspto-grants-2011_09
Patent number
US08022083B2

Reaction notes

Loading…