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

HRID 32992Notes

Reaction equation

HRID 32992 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][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:4]=1[CH2:21]C=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:31]([CH2:34][CH3:35])[CH:32]=[O:33])C=CC=CC=1.[C:48]1(C)C=CC=CC=1>>[CH2:34]([C:31](=[CH:48][CH2:21][C:4]1[C:5]([O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:18])[CH3:19])=[C:6]2[C:10](=[C:11]([CH3:12])[C:3]=1[O:2][CH3:1])[CH2:9][O:8][C:7]2=[O:13])[CH:32]=[O:33])[CH3:35]

Participants

4

Reactant 3

HCID 1140TolueneHCID 45855922-(Triphenylphosphoranylidene)butyraldehyde2×HCID 57478686[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-acetaldehyde

Product 1

HCID 765461992-Ethyl-4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-but-2-enalYield 83%

Procedure

A solution of [6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-acetaldehyde (1.5 g, 4.46 mmol) in toluene (14 mL) was heated at 100° C. with 2-(triphenyl-phosphanylidene)-butyraldehyde (1.68 g, 5.35 mmol) overnight. A second portion of 2-(triphenyl-phosphanylidene)-butyraldehyde (495 mg, 1.49 mmol) was added and the reaction mixture was heated for an additional day. After concentration, the residue was purified by silica gel chromatography to provide 1.3 g (83%) of the desired product as oil. 1H NMR (300 MHz, CDCl3) δ 0.01 (s, 9H), 1.03 (t, 3H), 1.10-1.21 (m, 2H), 2.15 (s, 3H), 2.15-2.44 (m, 2H), 3.67-3.76 (m, 2H), 3.74 (s, 3H), 4.31-4.36 (m, 2H), 5.10 (s, 2H), 6.34-6.38 (m, 1H), 9.28 (s, 1H) ppm.

Workup

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

Sources & evidence

ORD record
ord-a4e41557fcda47cbb5e5c4304101d2f1
Source dataset
uspto-grants-2008_09
Patent number
US07427636B2

Reaction notes

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