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Carbon tetrabromide → 6-(4-Bromo-3-methyl-but-2-enyl)-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

HRID 2282045
ノート
印刷プレビュー

反応式

HRID 2282045 の反応式
[CH2:1]([C:3]1[C:4]([CH3:26])=[C:5]2[C:9](=[C:10]([O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:11]=1[CH2:12][CH:13]=[C:14]([CH3:17])[CH2:15]O)[C:8](=[O:25])[O:7][CH2:6]2)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:47]>C(Cl)Cl>[Br:47][CH2:15][C:14]([CH3:17])=[CH:13][CH2:12][C:11]1[C:10]([O:18][CH2:19][CH2:20][Si:21]([CH3:23])([CH3:24])[CH3:22])=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[O:25])=[C:4]([CH3:26])[C:3]=1[CH2:1][CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 670098805-Ethyl-6-(4-hydroxy-3-methyl-but-2-enyl)4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one

生成物 1

HCID 670113116-(4-Bromo-3-methyl-but-2-enyl)-5-ethyl-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one収率 87%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

5-Ethyl-6-(4-hydroxy-3-methyl-but-2-enyl)-4-methyl-7-(2-trimethylsilanyl-ethoxy)-3H-isobenzofuran-1-one (57.2 mg, 0.152 mmol) was dissolved in DCM (3.5 mL). Polymer-bound triphenylphosphine (3 mmol/g, 152.1 mg) was added and the mixture was mechanically stirred at room temperature. Carbon tetrabromide (151.3 mg, 0.456 mmol) was added and the solution was stirred at room temperature. After 2 hrs, the reaction was filtered and the solvent was removed in vacuo. The crude material was purified by silica gel chromatography to provide 58.0 mg (87%) of the desired product. 1H NMR (300 MHz, CDCl3): δ=0.04 (s, 9H), 1.15 (t, J=7.8 Hz, 3H), 1.25 (m, 2H), 1.95 (s, 3H), 2.20 (s, 3H), 2.70 (q, J=7.8 Hz, 2H), 3.52 (d, J=6.3 Hz, 2H), 3.94 (s, 2H), 4.28 (m, 2H), 5.14 (s, 2H), 5.50 (m, 1H) ppm.

後処理

  1. stirringthe solution was stirred at room temperature
  2. filtrationthe reaction was filtered
  3. customthe solvent was removed in vacuo
  4. customThe crude material was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-66f5533fcdf24b039cdd3178d6d2413c
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09139604B2

反応ノート

読み込み中…

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