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

HRID 33631

反応式

HRID 33631 の反応式
[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]([CH3:34])[CH:32]=[O:33])C=CC=CC=1.[C:47]1(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][CH2:16][Si:17]([CH3:18])([CH3:20])[CH3:19])[C:4]=1[CH2:21][CH:47]=[C:31]([CH3:34])[CH:32]=[O:33]

参加物

4

反応物 3

HCID 1140TolueneHCID 42809872-(Triphenylphosphoranylidene)propionaldehyde2 回HCID 57478686[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-acetaldehyde

生成物 1

HCID 765461944-[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enal収率 83%

実験手順

[6-Methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-acetaldehyde (70 mg, 0.21 mmol) in toluene (2 mL) was heated at 100° C. with 2-(triphenyl-phosphanylidene)-propionaldehyde (72.9 mg, 0.23 mmol) overnight. A second portion of 2-(triphenyl-phosphanylidene)-propionaldehyde (33 mg, 0.11 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 54 mg (83%) of the desired product as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 0.00 (s, 9H), 1.10-1.21 (m, 2H), 1.87 (s, 3H), 2.16 (s, 3H), 3.67-3.76 (m, 2H), 3.74 (s, 3H), 4.27-4.39 (m, 2H), 5.11 (s, 2H), 6.40-6.48 (m, 1H), 9.2 (s, 1H) ppm.

後処理

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

出典と根拠

ORDレコード
ord-37fd65a422ab42239038f481362cf9d4
出典データセット
uspto-grants-2008_09
特許番号
US07429565B2

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