Triphenylphosphine → t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene

HRID 325032

반응식

HRID 325032 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:32]([O:36][C:37]([NH:39][C:40]1[C:41]([CH3:47])=[C:42]([OH:46])[CH:43]=[CH:44][CH:45]=1)=[O:38])([CH3:35])([CH3:34])[CH3:33].[C:48]([C:50]1[CH:55]=[CH:54][C:53]([CH2:56][CH2:57]O)=[CH:52][CH:51]=1)#[N:49]>C1COCC1.O>[C:32]([O:36][C:37]([NH:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([O:46][CH2:57][CH2:56][C:53]2[CH:54]=[CH:55][C:50]([C:48]#[N:49])=[CH:51][CH:52]=2)[C:41]=1[CH3:47])=[O:38])([CH3:35])([CH3:34])[CH3:33]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylateHCID 220334873-t-Butoxycarbonylamino-2-methylphenol

생성물 1

HCID 22033517t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene수율 77%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Triphenylphosphine (1.31 g, 13.5 mmol) and diethylazodicarboxylate (1.7 mL) were dissolved in THF (20 mL) under nitrogen. After 15 minutes 3-t-butoxycarbonylamino-2-methylphenol (2.48 g; 11.1 mmol; from step (i) above) dissolved in THF (20 mL) and 2-(4-cyanophenyl)ethanol (1.9 g, 13 mmol) were added. After 5 days at room temperature water was added and the stirring continued for 30 minutes. The mixture was extracted with EtOAc. The organic phase was washed with water and brine, dried (MgSO4) and the solvent removed in vacuo. Purification by flash chromatography afforded 2.98 g (77%) of the sub-title compound.

후처리

  1. extractionThe mixture was extracted with EtOAc
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-7b47ae80fd18405c948537f60313a90d
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06221898B1

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