Vanillin → (4R,5R)-2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarbomethoxy-1,3-dioxolane

HRID 1491568

反応式

HRID 1491568 の反応式
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[C:12]([C@@H:16]([C@H:18]([C:20]([O:22][CH3:23])=[O:21])[OH:19])O)([O:14][CH3:15])=[O:13]>>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:2]2[O:19][C@@H:18]([C:20]([O:22][CH3:23])=[O:21])[C@H:16]([C:12]([O:14][CH3:15])=[O:13])[O:1]2)[CH:11]=[CH:10][C:8]=1[OH:9]

参加物

3

反応物 2

HCID 1183VanillinHCID 11851Dimethyl L-tartrate

生成物 1

HCID 54460002(4R,5R)-2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarbomethoxy-1,3-dioxolane

実験手順

In a fashion similar to that described for Example 3, vanillin and dimethyl L-tartrate were condensed to provide (4R, 5R)-2-(3-methoxy-4-hydroxy-phenyl)-4,5-dicarbomethoxy-1,3-dioxolane, mp 88°-90° C., [α]D25 -35.1° (c,0.1,methanol). 1H-NMR (CDCl3)δ7.20 (1H,d,J=1. 8 Hz), 7.06 (1H,dd,J=1.8 Hz and 8.2 Hz), 6.19 (1H,d,J=8.2 Hz), 6.08 (1H,s), 5.82 (1H, s), 4.96 (1H,d,J=3.8 Hz), 4.85 (1H,d,J=3.8 Hz), 3.91 (3H,s), 3.87 (3H,s), 3.84 (3H,s). IR (film) 3450, 1750, 1600, 1510, 1460, 1430 cm-1. Ms m/e (% abundance) 313(2), 312(12), 253(40), 168(84), 151(100), 124(22), 109(14), 59(18).

後処理

  1. customcondensed

出典と根拠

ORDレコード
ord-1c85d54a53a34ab488199b791066e7c5
出典データセット
uspto-grants-1994_12
特許番号
US05371069

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