2-Chlorobenzaldehyde → 2-(2-Chlorophenyl)-6-hydroxychroman-4-one

HRID 31285

反応式

HRID 31285 の反応式
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.[Cl:20]C1C=CC=CC=1C=O>CCCCCCC.C(OCC)(=O)C>[Cl:20][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[CH:8]1[CH2:17][C:16](=[O:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=2)[O:9]1

参加物

4

反応物 2

HCID 69962-ChlorobenzaldehydeHCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

生成物 1

HCID 179785332-(2-Chlorophenyl)-6-hydroxychroman-4-one

試薬・触媒・溶媒 1

HCID 21899848Ethylacetate heptane溶媒

実験手順

2-(2-Chlorophenyl)-6-hydroxychroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 3.0 g of 2 ′,5′-dihydroxyacetophenone and 2.8 g of 2-chlorobenzaldehyde. The product was passed though silica gel using heptane-ethyl acetate as an eluant and then triturated with ethanol. 1H NMR (400 MHz, d6-DMSO) δ: 9.49 (s, 1H), 7.77 (dd, 1H, J 7.7, 2.0 Hz), 7.53 (dd, 1H, J 7.6, 1.8 Hz), 7.49-7.41 (m, 2H), 7.14 (d, 1H, J 2.9 Hz), 7.06 (dd, 1H, J 8.8, 2.9 Hz), 6.93 (d, 1H, J 8.8 Hz), 5.78 (dd, 1H, J 13.6, 2.6 Hz), 3.19 (dd, 1H, J −16.9, 13.6 Hz), 2.78 (dd, 1H, J −16.9, 2.6 Hz).

後処理

  1. customtriturated with ethanol

出典と根拠

ORDレコード
ord-9ced01e7a76340c1b0318b39fecdf6eb
出典データセット
uspto-grants-2008_09
特許番号
US07425568B2

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