Triphenylphosphine → 3-Chloro-5-[2-(4-cyanophenyl)ethoxy]phenol

HRID 325051

反応式

HRID 325051 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:32][C:33]1[CH:38]=[C:37]([OH:39])[CH:36]=[C:35]([OH:40])[CH:34]=1.[C:41]([C:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH2:50]O)=[CH:45][CH:44]=1)#[N:42]>C(Cl)Cl.CCOCC>[Cl:32][C:33]1[CH:38]=[C:37]([OH:39])[CH:36]=[C:35]([O:40][CH2:50][CH2:49][C:46]2[CH:47]=[CH:48][C:43]([C:41]#[N:42])=[CH:44][CH:45]=2)[CH:34]=1

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 945541,3-Benzenediol, 5-chloro-HCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 220335343-Chloro-5-[2-(4-cyanophenyl)ethoxy]phenol収率 21.3%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

Triphenylphoshine (32 g; 122 mmol) and diethylazodicarboxylate (19.2 mL; 122 mmol) were dissolved in CH2Cl2 (150 mL). Chloro-3,5-dihydroxybenzene (9.1 g; 63 mmol; from step (i) above) and 2-(4-cyanophenyl)ethanol (9.04 g; 61 mmol) were added and the solution was stirred at room temperature overnight. The mixture was diluted with Et2O and filtered through Celite. The solvent was removed in vacuo. Purification, first by flash chromatography (SiO2; CH2Cl2:MeOH), then by preparative HPLC (60% CH3CN:0.1 M NH4OAc/aq), afforded 3.55 g (21%) of the sub-title compound.

後処理

  1. filtrationfiltered through Celite
  2. customThe solvent was removed in vacuo
  3. customPurification

出典と根拠

ORDレコード
ord-b142d67c5d7743cc8446130949fd67d9
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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