3-Methoxybenzaldehyde → 1-Hydroxy-7-methoxy-1,3-dihydrobenzo[c]furan

HRID 611699ノート

反応式

HRID 611699 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:10](=[O:11])[O:9][CH2:8]2.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19].C1(P(=CC(OC)=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl>[OH:11][CH:10]1[C:12]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[CH2:8][O:9]1.[OH:19][CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([O:14][CH3:13])[C:16]=1/[CH:3]=[CH:12]/[C:10]([O:9][CH3:8])=[O:11]

参加物

6

反応物 3

HCID 115693-MethoxybenzaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 109865837-methoxy-3H-isobenzofuran-1-one

生成物 2

HCID 136136891-Hydroxy-7-methoxy-1,3-dihydrobenzo[c]furanHCID 19598060Methyl 2E-3-(2-hydroxymethyl-6-methoxyphenyl)acrylate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
50 °C

実験手順

1-Hydroxy-7-methoxy-1,3-dihydrobenzo[c]furan (1.08 g), which was prepared with using 7-methoxyphthalide which was synthesized with using 3-methoxybenzaldehyde by the method described in Journal of Organic Chemistry, 1980, 45, 1835-1838, was dissolved in chloroform (20 ml). Methyl (triphenylphosphoranylidene)acetate (2.68 g) was added to the solution. The mixture was stirred for 40 min. at 50° C. A temperature of the reaction mixture was down to room temperature. The reaction solution was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (1.25 g) having the following physical data.

後処理

  1. customwas down to room temperature
  2. customThe reaction solution was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-9fd3965edade4969aa03492764cf90ed
出典データセット
uspto-grants-1999_12
特許番号
US06001877

反応ノート

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