Boron trifluoride etherate → HCID 15073127、化合物

HRID 1837083ノート

反応式

HRID 1837083 の反応式
B(F)(F)F.CC[O:7][CH2:8][CH3:9].OCC[C:13]#[C:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O.C(=O)(O)[O-:26].[Na+]>C(O)C1C=CC=CC=1.[Hg]=O>[CH2:18]([O:17][C:15]1[CH2:14][CH2:13][O:7][C:8](=[O:26])[CH:9]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

参加物

6

反応物 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 15073126Benzyl 5-hydroxypent-2-ynoate

生成物 1

HCID 15073127HCID 15073127、化合物収率 55%

試薬・触媒・溶媒 2

HCID 30856Mercuric oxide触媒HCID 244Benzyl Alcohol溶媒2 回

反応条件

温度
60 °C

実験手順

A heterogeneous mixture of benzyl alcohol (2.65 mole, 274.4 mL), mercury(II) oxide (red) (13.26 mmol, 2.87 g) and boron trifluoride diethyl etherate (0.133 mole, 16.3 mL) was heated at 60° C. for 3 hours (eventually turned homogeneous). A solution of the product from Example 31C (90.17 g, 0.442 mole) in benzyl alcohol (91.5 mL) was added at ambient temperature, and the reaction mixture was stirred at 70° C. for 4 hours and again at ambient temperature overnight. It was poured into an aqueous saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified via flash chromatography (silica, hexane to hexane:ethyl acetate, 30:1 to 1:2) to provide the title compound as a white solid (49.6 g, 55%). 1H NMR (300 MHz, CDCl3) δ 2.60 (t, 2H), 4.38 (t, 2H), 4.95 (s, 2H), 5.28 (s, 1H), 7.32-7.46 (m, 5H).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via flash chromatography (silica, hexane to hexane:ethyl acetate, 30:1 to 1:2)

出典と根拠

ORDレコード
ord-c632c3d6c3e6420f99d07531fffe3a8b
出典データセット
uspto-grants-2004_08
特許番号
US06780872B2

反応ノート

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