5H-Dibenzo[a,d]cyclohepten-5-one → 5-(2,4-bis(1,1-dimethylethoxy)pyrimidin-5-yl)-5H-dibenzo[a,d]cyclohepten-5-ol

HRID 1531913

반응식

HRID 1531913 반응식
Br[C:2]1[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:4][C:5]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[N:6][CH:7]=1.C([Li])CCC.[CH:23]1[C:33]2[CH:32]=[CH:31][C:30]3[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=3[C:28](=[O:38])[C:27]=2[CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:10][C:9]([CH3:12])([O:8][C:5]1[N:4]=[C:3]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:2]([C:28]2([OH:38])[C:29]3[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=3[CH:31]=[CH:32][C:33]3[CH:23]=[CH:24][CH:25]=[CH:26][C:27]2=3)=[CH:7][N:6]=1)[CH3:11]

참가 물질

6

반응물 4

HCID 166795H-Dibenzo[a,d]cyclohepten-5-oneHCID 25517Ammonium ChlorideHCID 8188515-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidineHCID 178418339Butyllithium

생성물 1

HCID 212508825-(2,4-bis(1,1-dimethylethoxy)pyrimidin-5-yl)-5H-dibenzo[a,d]cyclohepten-5-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of the product of step (i) (50 g) in dry tetrahydrofuran (11) at −78° C. was added n-butyllithium (69 ml of a 2.5 M solution in hexanes) dropwise. After 0.5 hours a solution of 5H-dibenzo[a,d]cyclohepten-5-one (44 g) in tetrahydrofuran (100 ml) was added. The reaction mixture was stirred at −78° C. for three hours and then allowed to warm to room temperature overnight. Saturated aqueous ammonium chloride solution (400 ml) was added and the mixture extracted with ethyl acetate. The organic solution was dried (MgSO4) and evaporated under reduced pressure to give the crude 5-[2,4-bis[1,1-dimethylethoxy]pyrimidin-5-yl]-5H-dibenzo[a,d]cyclohepten-5-ol which was used directly.

후처리

  1. temperatureto warm to room temperature overnight
  2. extractionthe mixture extracted with ethyl acetate
  3. dry with materialThe organic solution was dried (MgSO4)
  4. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-b67e701fdc6a4dd4ae5231942ef25189
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06200981B1

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