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

HRID 540719Notes

Reaction equation

HRID 540719 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-e0d005541f7547f2964c0027cc10805d
Source dataset
uspto-grants-2014_10
Patent number
US08871785B2

Reaction notes

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