Ammonium Chloride → 2-[(1RS,2SR)-1-hydroxy-2-[(3-methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazole

HRID 377302노트

반응식

HRID 377302 반응식
O1CCCC1.C([N-]C(C)C)(C)C.[Li+].[C:14]1([C:20]2[N:21]=[CH:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:31][O:32][C:33]1[CH:34]=[C:35]([CH2:39][CH:40]2[CH2:45][CH2:44][CH2:43][CH2:42][C:41]2=[O:46])[CH:36]=[CH:37][CH:38]=1.[Cl-].[NH4+]>C1CCCCC1.O1CCCC1.C(OCC)C.C(Cl)(Cl)(Cl)Cl>[OH:46][C:41]1([C:22]2[O:23][C:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[C:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:21]=2)[CH2:42][CH2:43][CH2:44][CH2:45][CH:40]1[CH2:39][C:35]1[CH:36]=[CH:37][CH:38]=[C:33]([O:32][CH3:31])[CH:34]=1

참가 물질

9

반응물 4

HCID 25517Ammonium ChlorideHCID 6134984,5-DiphenyloxazoleHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)HCID 148680162-(3-Methoxy-benzyl)-cyclohexanone

생성물 1

HCID 184591732-[(1RS,2SR)-1-hydroxy-2-[(3-methoxyphenyl)methyl]cyclohexyl]-4,5-diphenyloxazole수율 37.6%

시약·촉매·용매 4

HCID 3283Diethyl Ether용매HCID 5943Carbon Tetrachloride용매HCID 8028Tetrahydrofuran용매2회HCID 8078Cyclohexane용매

실험 절차

A 1.5 M solution of lithium diisopropylamide mono(tetrahydrofuran) in cyclohexane (19.9 ml) was added dropwise to a stirred solution of 4,5-diphenyloxazole (6.0 g) in tetrahydrofuran (36 ml) and diethyl ether (18 ml) under dry ice--carbon tetrachloride cooling and the mixture was stirred at the same temperature for a while and at 0° C. for a while. A solution of 2-[(3-methoxyphenyl)methyl]cyclohexanone (5.92 g) in tetrahydrofuran (16 ml) was added to the reaction mixture under dry ice-acetone cooling, and the resulting mixture was stirred at the same temperature for several hours. Then the reaction temperature was allowed to rise gradually to room temperature and the reaction mixture was allowed to stand at room temperature overnight. The mixture was treated with ammonium chloride aqueous solution and partitioned between ethyl acetate and 1N hydrochloric acid. The ethyl acetate layer was separated and washed successively with 1N hydrochloric acid (twice), sodium bicarbonate aqueous solution, and brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was chromatographed (n-hexane - ethyl acetate (10:1)) over silica gel. The first eluate afforded 2-[(1RS,2RS)-1-hydroxy-2-[(3-methoxyphenyl)methyl]-cyclohexyl]-4,5-diphenyloxazole (4.48 g) as pale yellow paste.

후처리

  1. customto rise gradually to room temperature
  2. custompartitioned between ethyl acetate and 1N hydrochloric acid
  3. customThe ethyl acetate layer was separated
  4. washwashed successively with 1N hydrochloric acid (twice), sodium bicarbonate aqueous solution, and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe oily residue was chromatographed (n-hexane - ethyl acetate (10:1)) over silica gel

출처 및 근거

ORD 기록
ord-aba60a4d061d43c2988a38106c09ab94
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06025375

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