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

HRID 2293678ノート

反応式

HRID 2293678 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-2c5a7267544148f3b60aa14a06517759
出典データセット
uspto-grants-1997_11
特許番号
US05686486

反応ノート

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