反応式
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.C([O:22][C:23]1[C:24](=[O:39])[O:25][CH:26]([CH2:36][CH2:37]O)[C:27]=1[O:28]CC1C=CC=CC=1)C1C=CC=CC=1>>[CH:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[O:6][C:5]=2[CH:13]=[CH:14][C:2]=1[O:1][CH2:37][CH2:36][CH:26]1[O:25][C:24](=[O:39])[C:23]([OH:22])=[C:27]1[OH:28]参加物
実験手順
Mitsunoble coupling of 0.22 g (1.2 mmol) of 2-hydroxydibenzofuran with 0.34 g (1.0 mmol) of 3,4-dibenzyloxy-5-(2-hydroxyethyl)-2(5H)-furanone and subsequent benzyl group deprotection by hydrogenation were performed in a similar manner as described in the synthesis of 3,4-dihydroxy-5-[2-(4-phenoxy)phenoxyethyl]-2(5H)-furanone to provide 40 mg (10% yield) of 5-[2-(dibenzofuran-2-oxy)ethyl]-3,4-dihydroxy-2(5H)-furanone a white solid.: mp 191-192° C. (ether/hexanes), 1H NMR (acetone-d6) δ 8.23-8.18 (m, 1H), 7.83-7.44 (m, 5H), 7.28-7.23 (m, 1H), 5.12 (dd, J=5.3, 8.7 Hz, 1H), 4.42 (dd, J=2.6, 4.7 Hz, 2H), 2.69-2.59 (m, 1H), 2.21-2.08 (m, 1H). 13C NMR (acetone-d6) δ 169.68, 157.31, 155.75, 153.70, 151.31, 127.76, 125.05, 124.83, 123.07, 121.34, 118.46, 116.42, 112.39, 111.90, 105.40, 72.72, 64.57, 32.64. Anal Calcd for C18H14O6 +0.25 H2O: C, 65.36; H, 4.57. Found: C, 65.52; H, 4.23.
出典と根拠
- ORDレコード
- ord-21caa20e277d41208181557179468cdd
- 出典データセット
- uspto-grants-2000_10
- 特許番号
- US06136832
関連ノート
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