Boron trifluoride etherate → 4-Hydroxy-3-(1-(1-naphthyl)-propyl)-coumarin

HRID 2293678노트

반응식

HRID 2293678 반응식
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.[C:13]1([CH:23](O)[CH2:24][CH3:25])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.B(F)(F)F.CCOCC>O1CCOCC1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[C:3]=1[CH:23]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1)[CH2:24][CH3:25]

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 124533351-(1-Naphthyl)-1-propanolHCID 546829304-Hydroxycoumarin

생성물 1

HCID 547115754-Hydroxy-3-(1-(1-naphthyl)-propyl)-coumarin수율 51%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a cloudy solution of 324 mg of 4-hydroxycoumarin and 373 mg of 1-(1-naphthyl)-propan-1-ol of Preparation 22 in 7 mL of dioxane under an argon atmosphere is added 0.85 mL of boron trifluoride etherate. After stirring overnight the resulting yellow solution is concentrated under reduced pressure. The residue is partioned between water and ethyl acetate; the organic phase is washed with brine, dried (magnesium sulfate), and concentrated. The residue is adsorbed onto silica gel and then flashed column chromatographed using 40% to 50% ethyl acetate in hexane to yield 337 mg of the title product as a pale yellow solid. An analytical sample may be prepared by crystallization from ethyl acetate-hexanes.

후처리

  1. concentrationis concentrated under reduced pressure
  2. washthe organic phase is washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customchromatographed

출처 및 근거

ORD 기록
ord-2c5a7267544148f3b60aa14a06517759
출처 데이터셋
uspto-grants-1997_11
특허 번호
US05686486

반응 노트

불러오는 중…