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

HRID 33667노트

반응식

HRID 33667 반응식
[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(C)C=[O:33])C=CC=CC=1.[C:47]1([CH3:53])[CH:52]=CC=[CH:49][CH:48]=1>>[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]([CH3:18])([CH3:19])[CH3:20])[C:4]=1[CH2:49][CH:48]=[C:47]([CH3:53])[CH:52]=[O:33])[CH3:2]

참가 물질

4

반응물 3

HCID 1140TolueneHCID 42809872-(Triphenylphosphoranylidene)propionaldehydeHCID 59794521[6-Ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro isobenzofuran-5-yl]-acetaldehyde

생성물 1

HCID 725636044-[6-Ethyl-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enal수율 77%

실험 절차

[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)-propionaldehyde (72.9 mg, 0.23 mmol) in toluene (3 mL) were heated at 100° C. After 15 hours, a second portion of 2-(triphenyl-phosphanylidene)-propionaldehyde (33 mg, 0.11 mmol) was added and the reaction mixture was heated for additional 9 hours. The toluene was removed in vacuo, and the residue was purified by silica gel chromatography to provide 77.6 mg (77%) of the desired product as a pale yellow oil. 1H NMR (300 MHz, CDCl3): δ=0.03 (s, 9H), 1.15 (t, J=7.5 Hz, 3H), 1.21 (m, 2H), 1.93 (s, 3H), 2.21 (s, 3H), 2.71 (q, J=7.5 Hz, 2H), 3.82 (d, J=6.9 Hz, 2H), 4.34 (m, 2H), 5.18 (s, 2H), 6.38 (m, 1H), 9.35 (s, 1H) ppm.

후처리

  1. temperaturethe reaction mixture was heated for additional 9 hours
  2. customThe toluene was removed in vacuo
  3. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-191c6bacf17a4d05ab7c414e2426e14a
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429565B2

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