(3,5-Diethoxy-4-pyrrol-1-yl-phenyl)-methanol → 3,5-diethoxy-4-(1H-pyrrol-1-yl)benzaldehyde

HRID 502373

反応式

HRID 502373 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:18][OH:19])[CH:7]=[C:8]([O:15][CH2:16][CH3:17])[C:9]=1[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)[CH3:2]>C1(C)C=CC=CC=1.O=[Mn]=O>[CH2:16]([O:15][C:8]1[CH:7]=[C:6]([CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:9]=1[N:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)[CH:18]=[O:19])[CH3:17]

参加物

4

反応物 1

HCID 66912179(3,5-Diethoxy-4-pyrrol-1-yl-phenyl)-methanol

生成物 1

HCID 534860133,5-diethoxy-4-(1H-pyrrol-1-yl)benzaldehyde収率 89.1%

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 1140Toluene溶媒

実験手順

To a solution of 3,5-diethoxy-4-pyrrol-1-yl-benzoic acid ethyl ester (1.51 g, 4.98 mmol) in toluene (5 mL) was added slowly over a time period of 15 min under slight cooling to 20° C. a solution of diisobutylaluminium hydride (8.9 mL, 12.45 mmol, 20% solution in toluene). After 1 h, the excess hydride was quenched by cautious addition of water (10 mL) and a 28% solution of sodium hydoxide (2 mL). The mixture was stirred for 30 min and the organic phase filtered over Hyflo. The aqueous layer was extracted with toluene (2×50 mL), the combined organic phases washed with a sat. solution of sodium chloride (2×50 mL) and concentrated by evaporation under reduced pressure to afford 1.30 g (100%) of (3,5-diethoxy-4-pyrrol-1-yl-phenyl)-methanol. The crude alcohol (1.30 g, 4.98 mmol, 1.0 equiv) was dissolved in toluene (20 mL) and MnO2 (7.79 g, 89.5 mmol, 18.0 equiv) was added. The reaction mixture was heated to reflux for 7 h, after which time the reaction was filtered through Hyflo and concentrated yielding 1.15 g (89% yield) of the title compound.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 7 h
  3. filtrationafter which time the reaction was filtered through Hyflo
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-33f8e63675fc442a98536be6bbb72f83
出典データセット
uspto-grants-2010_08
特許番号
US07772253B2

関連ノート

読み込み中…