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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
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인쇄 미리보기

반응식

HRID 2282045 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-66f5533fcdf24b039cdd3178d6d2413c
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09139604B2

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