Trifluoroacetic acid → 5-Bromo-7-isopropyl-3,3,6-trimethyl-2,3-dihydro-benzofuran

HRID 2290149노트

반응식

HRID 2290149 반응식
[Br:1][C:2]1[C:3]([CH3:17])=[C:4]([C:13](O)([CH3:15])[CH3:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl.O.CO>[Br:1][C:2]1[C:3]([CH3:17])=[C:4]([CH:13]([CH3:14])[CH3:15])[C:5]2[O:9][CH2:8][C:7]([CH3:10])([CH3:11])[C:6]=2[CH:12]=1

참가 물질

8

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 186991752-(5-Bromo-3,3,6-trimethyl-2,3-dihydro-benzofuran-7-yl)-propan-2-ol2회

생성물 1

HCID 186991975-Bromo-7-isopropyl-3,3,6-trimethyl-2,3-dihydro-benzofuran수율 95.5%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A stirred, cooled (ice bath)solution of 2-(5-bromo-3,3,6-trimethyl-2,3-dihydro-benzofuran-7-yl)-propan-2-ol (Compound 49, 1.51 g, 5.03 mmol) in 15 mL of dichloromethane was treated with triethyl silane (1.4 mL, 8.76 mmol) followed by trifluoroacetic acid (0.65 mL, 8.43 mmol) and the resulting clear, colorless solution was stirred at ambient temperature overnight. The reaction mixture was cooled, treated with 6 mL each of methanol and water, neutralized cautiously with saturated sodium bicarbonate solution and extracted with diethylether. The organic extract was dried over anhydrous sodium sulfate, filtered and evaporated to an oil. Flash column chromatography using 0.5% ethyl acetate in hexanes as the eluent afforded the title compound (1.36 g, 95%) as an oil. 1H NMR (300 MHz, CDCl3): δ 7.11 (s, 1H), 4.18 (s, 2H), 3.25 (heptet, 1H, J=7.1 Hz), 2.40 (s, 3H), 1.30 (s, 6H), 1.31 (d, 6H, J=7.1 Hz).

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with diethylether
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated to an oil

출처 및 근거

ORD 기록
ord-44bf681f6b134a7f9268fa6a72c31de1
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06093838

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