Boron trifluoride etherate → HCID 15073127, 화합물

HRID 1837083노트

반응식

HRID 1837083 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 15073127HCID 15073127, 화합물수율 55%

시약·촉매·용매 2

HCID 30856Mercuric oxide촉매HCID 244Benzyl Alcohol용매2회

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c632c3d6c3e6420f99d07531fffe3a8b
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06780872B2

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