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

HRID 31199

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.O[C:21]1C=CC(O)=C[C:22]=1C(=O)C.C(C1C=CC(C=O)=CC=1)C>>[CH2:21]([C:7]1[CH:6]=[CH:5][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:3][CH:2]=1)[CH3:22]

참가 물질

반응물 3

HCID 102792-Acetylhydroquinone

HCID 208614-Ethylbenzaldehyde

HCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

생성물 1

HCID 179785782-(4-Ethylphenyl)-6-hydroxychroman-4-one

실험 절차

2-(4-Ethylphenyl)-6-hydroxychroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 1.0 g of 2′,5′-dihydroxyacetophenone and 0.8 ml of 4-ethylbenzaldehyde. The product was recrystallised from acetic acid. 1H NMR (400 MHz, d6-DMSO) δ: 7.43 (d, 2H, J 8.1 Hz), 7.25 (d, 2H, J 8.1 Hz), 7.11 (d, 1H, J 3.1 Hz), 7.03 (dd, 1H, J 8.9, 3.1 Hz), 6.93 (d, 1H, J 8.9 Hz), 5.51 (dd, 1H, J 13.0, 2.9 Hz), 3.15 (dd, 1H, J −16.9, 13.0 Hz), 2.75 (dd, 1H, J −16.9, 2.9 Hz), 2.62 (q, 2H, J 7.5 Hz), 1.18 (t, 3H, J 7.5 Hz).

후처리

customThe product was recrystallised from acetic acid

출처 및 근거

ORD 기록: ord-0087bc3fa7be43928f98a0a630d52ca8
출처 데이터셋: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07425568B2

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