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

HRID 355414노트

반응식

HRID 355414 반응식
[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]

참가 물질

4

반응물 2

HCID 81566Ethyl stearoylacetateHCID 108445152,4-Difluororesorcinol2회

생성물 1

HCID 57067496,8-Difluoro-4-heptadecyl-7-hydroxycoumarin수율 11.2%

시약·촉매·용매 1

HCID 6395Methanesulfonic Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8b46a6f2918a46c1ad688fd1a3b30920
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830912

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