2-(1,3-Dioxolan-2-yl)-3-[1-hydroxy-1-(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene → 2-Formyl-3-[(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

HRID 1836889ノート

反応式

HRID 1836889 の反応式
[O:1]1CCO[CH:2]1[C:6]1[C:15]([CH:16](O)[C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[CH:14][C:13]2[C:12]([CH3:24])([CH3:23])[CH2:11][CH2:10][C:9]([CH3:26])([CH3:25])[C:8]=2[CH:7]=1>C(OCC)(=O)C.[Pd]>[CH:2]([C:6]1[C:15]([CH2:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[CH:14][C:13]2[C:12]([CH3:24])([CH3:23])[CH2:11][CH2:10][C:9]([CH3:26])([CH3:25])[C:8]=2[CH:7]=1)=[O:1]

参加物

4

反応物 1

HCID 234989602-(1,3-Dioxolan-2-yl)-3-[1-hydroxy-1-(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

生成物 1

HCID 234989152-Formyl-3-[(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene収率 62%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

The alcohol prepared above was dissolved in 7 mL of ethyl acetate and 75 mg of 10% Pd/C was added and the reaction mixture stirred under a hydrogen atmosphere for about 4 hours. The reaction mixture was filtered through Celite and concentrated in vacuo. The resulting residue was purified by preparative thin layer chromatography (10% ethyl acetate/hexane) to give 2-formyl-3-[(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (94 mg, 62%) directly.

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified by preparative thin layer chromatography (10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-0b4238cb6de846cab46470d87d26fd41
出典データセット
uspto-grants-2004_08
特許番号
US06777418B2

反応ノート

読み込み中…