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Boron trifluoride etherate → 4-Bromo-7-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxaldehyde diethy acetal

HRID 728572
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HRID 728572 반응식
[CH:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])OCC.B(F)(F)F.CCOCC.[Br:20][C:21]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]2[C:22]=1[CH2:23][CH2:24][C:25]2=[O:32].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:9]([O:8][CH:1]([O:5][CH2:6][CH3:7])[CH:24]1[CH2:23][C:22]2[C:26](=[C:27]([O:30][CH3:31])[CH:28]=[CH:29][C:21]=2[Br:20])[C:25]1=[O:32])[CH3:10]
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참가 물질

6

반응물 4

HCID 8000Boron trifluoride etherateHCID 31214Ethyl orthoformateHCID 81531DiisopropylethylamineHCID 2233794-Bromo-7-methoxy-1-indanone

생성물 1

HCID 104501054-Bromo-7-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxaldehyde diethy acetal

시약·촉매·용매 1

HCID 6344Dichloromethane
용매
2회

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온도
0 °C

실험 절차

Triethyl orthoformate (16.5 ml) was cooled to -30° C. and 15.0 ml BF3.Et2O in 50 ml methylene chloride was added. The reaction was warmed to 0° C. for 15 min, and then cooled to -78° C. To the reaction was added 12.05 g of the product from Example 34 in 50 ml methylene chloride, followed by dropwise addition of 19.4 ml diisopropyl ethyl amine. The reaction was then warmed to -15° C. for 2 h, then quenched in 5% NaHCO3 solution and extracted with methylene chloride. The organic extracts were washed with brine, dried (MgSO4), and the solvent removed. The crude product was triturated with cold hexane, and the crystalline product collected to yield 14.60 g of a white solid, mp: 76-8° C. NMR (CDCl3) δ 1.05 (t, 3H), 1.27 (t, 3H), 3.03 (m, 2H), 3.30 (m, 1H), 3.43-3.80 (m, 4H), 3.95 (s, 3H), 5.00 (d, 1H), 6.71 (d, 1H), 7.63 (d, 1H).

후처리

  1. temperaturecooled to -78° C
  2. temperatureThe reaction was then warmed to -15° C. for 2 h
  3. customquenched in 5% NaHCO3 solution
  4. extractionextracted with methylene chloride
  5. washThe organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed
  8. customThe crude product was triturated with cold hexane
  9. customthe crystalline product collected

출처 및 근거

ORD 기록
ord-4303486fcb3f4e2a883e5f1a1fe804cf
출처 데이터셋
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05049564

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