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

HRID 325051

반응식

HRID 325051 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-b142d67c5d7743cc8446130949fd67d9
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06221898B1

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