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

HRID 2290149ノート

反応式

HRID 2290149 の反応式
[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

参加物

8

反応物 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 186991752-(5-Bromo-3,3,6-trimethyl-2,3-dihydro-benzofuran-7-yl)-propan-2-ol2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-44bf681f6b134a7f9268fa6a72c31de1
出典データセット
uspto-grants-2000_07
特許番号
US06093838

反応ノート

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