Ethyl stearoylacetate → 6,8-Difluoro-4-heptadecyl-7-hydroxycoumarin

HRID 355414ノート

反応式

HRID 355414 の反応式
[F:1][C:2]1[C:8]([OH:9])=[C:7]([F:10])[CH:6]=[CH:5][C:3]=1[OH:4].[C:11]([CH2:30][C:31](OCC)=[O:32])(=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CS(O)(=O)=O>[F:10][C:7]1[CH:6]=[C:5]2[C:3](=[C:2]([F:1])[C:8]=1[OH:9])[O:4][C:31](=[O:32])[CH:30]=[C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

参加物

4

反応物 2

HCID 81566Ethyl stearoylacetateHCID 108445152,4-Difluororesorcinol2 回

生成物 1

HCID 57067496,8-Difluoro-4-heptadecyl-7-hydroxycoumarin収率 11.2%

試薬・触媒・溶媒 1

HCID 6395Methanesulfonic Acid溶媒

実験手順

A mixture of 2,4-difluororesorcinol (Compound 4, 0.15 g, 1.0 mmol) and ethyl stearoylacetate (354 mg, 1.03 mmol) in methanesulfonic acid (4 mL) is stirred at room temperature overnight. The reaction mixture is partitioned between ethyl acetate and water. The ethyl acetate layer is washed with brine (1×) and dried over sodium sulfate, then concentrated to 0.67 g of a pale brown solid, which is purified by silica gel chromatography to give 49 mg of Compound 30 as a colorless powder: Rf =0.64 (EtOAc/hexanes 3:2). 1H NMR (CDCl3) δ 7.12 (dd, 1H), 6.22 (s, 1H), 1.7-0.7 (m, 70H). 19F NMR (CDCl3) Φ 139.8 (t, 1F), 153.5 (d, 1F).

後処理

  1. customThe reaction mixture is partitioned between ethyl acetate and water
  2. washThe ethyl acetate layer is washed with brine (1×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to 0.67 g of a pale brown solid, which
  5. customis purified by silica gel chromatography

出典と根拠

ORDレコード
ord-8b46a6f2918a46c1ad688fd1a3b30920
出典データセット
uspto-grants-1998_11
特許番号
US05830912

反応ノート

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