2-Acetylhydroquinone → 2-(4-Trifluoromethylphenyl)-6-hydroxychroman-4-one

HRID 31269

반응식

HRID 31269 반응식
F[C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=3)[O:9]2)[CH:5]=[CH:6][CH:7]=1.OC1C=CC(O)=CC=1C(=O)C.[F:31][C:32]([F:42])([F:41])C1C=CC(C=O)=CC=1>>[OH:19][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[O:9][CH:8]([C:4]1[CH:5]=[CH:6][C:7]([C:32]([F:42])([F:41])[F:31])=[CH:2][CH:3]=1)[CH2:17][C:16]2=[O:18]

참가 물질

4

반응물 3

HCID 102792-AcetylhydroquinoneHCID 679964-(Trifluoromethyl)benzaldehydeHCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

생성물 1

HCID 179785102-(4-Trifluoromethylphenyl)-6-hydroxychroman-4-one

실험 절차

6-Hydroxy-2-(4-trifluoromethylphenyl)chroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 2.0 g of 2′,5′-dihydroxyacetophenone and 2.1 ml of 4-trifluoromethylbenzaldehyde. The product was purified by column chromatography using heptane-ethyl acetate (2:1) as an eluant. Further purification was carried out by column chromatography using toluene-ethyl acetate (4:1) as an eluant. Finally the product was crystallised from ethanol. 1H NMR (400 MHz, d6-DMSO) δ: 9.47 (s, 1H), 7.82-7.76 (m, 4H), 7.13 (d, 1H, J 3.0 Hz), 7.06 (dd, 1H, J 8.8, 3.0 Hz), 6.99 (d, 1H, J 8.8 Hz), 5.70 (dd, 1H, J 12.9, 2.9 Hz), 3.16 (dd, 1H, J −16.9, 12.9 Hz), 2.86 (dd, 1H, J −16.9, 2.9 Hz).

후처리

  1. customThe product was purified by column chromatography
  2. customFurther purification
  3. customFinally the product was crystallised from ethanol

출처 및 근거

ORD 기록
ord-4e14c0209b2b43c2b7468fcad7bfe3c5
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425568B2

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