Orcinol → 3-[2-(4-Cyanophenyl)ethoxy]-5-methylphenol

HRID 325049

反応式

HRID 325049 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C:21]1[CH:22]=[C:23]([CH3:28])[CH:24]=[C:25]([OH:27])[CH:26]=1.[C:29]([C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38]O)=[CH:33][CH:32]=1)#[N:30].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:29]([C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][O:20][C:21]2[CH:26]=[C:25]([OH:27])[CH:24]=[C:23]([CH3:28])[CH:22]=2)=[CH:33][CH:32]=1)#[N:30]

参加物

6

反応物 4

HCID 10436OrcinolHCID 11776TriphenylphosphineHCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 220335303-[2-(4-Cyanophenyl)ethoxy]-5-methylphenol収率 37%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Triphenylphoshine (7.86 g; 30 mmol), 3,5-dihydroxytoluene (2.5 g; 20 mmol) and 2-(4-cyanophenyl)ethanol (4.41 g; 30 mmol) were dissolved in THF (50 mL). Diethylazodicarboxylate (5.22 g; 30 mmol; dissolved in THF (10 mL)), was added and the solution was stirred at room temperature overnight. The solvent was removed in vacuo and the white solid residue extracted with Et2O. Purification by flash chromatography (SiO2; toluene:EtOAc (10:1)) afforded 1.85 g (37%) of the sub-title compound as a white solid.

後処理

  1. customThe solvent was removed in vacuo
  2. extractionthe white solid residue extracted with Et2O
  3. customPurification by flash chromatography (SiO2; toluene:EtOAc (10:1))

出典と根拠

ORDレコード
ord-c75018db129c4a1882a1a70317255148
出典データセット
uspto-grants-2001_04
特許番号
US06221898B1

関連ノート

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