Ethyl Acetate → ethyl (R)-{3-{[2-(4,5-diphenyloxazole-2-yl)-1-hydroxy-2-cyclohexen-1-yl]methyl}phenoxy}-acetate

HRID 379319노트

반응식

HRID 379319 반응식
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@:19]([O:49][Si](C)(C)C)([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([O:31][Si](C(C)(C)C)(C5C=CC=CC=5)C5C=CC=CC=5)[CH:26]=4)[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:72][CH2:73][O:74][C:75]([CH3:77])=[O:76]>C1COCC1>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@@:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=4)[O:31][CH2:77][C:75]([O:74][CH2:73][CH3:72])=[O:76])([OH:49])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 15550206(R)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyloxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]-2-cyclohexene

생성물 1

HCID 15550207ethyl (R)-{3-{[2-(4,5-diphenyloxazole-2-yl)-1-hydroxy-2-cyclohexen-1-yl]methyl}phenoxy}-acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (R)-2-(4,5-diphenyloxazol-2-yl)-1-trimethylsilyloxy-1-[3-(tertbutyldiphenylsiloxy)benzyl]-2-cyclohexene (10 g) in THF (50 ml) was added tetrabutylammonium fluoride (41 ml, 1M solution in THF) at room temperature. After being stirred for 4 hours, the mixture was diluted with EtOAc. The mixture was washed with 1N-HCl solution and brine and evaporated. The residue was dissolved in DMF (50 ml), followed by addition of K2CO3 (5 g) and ethyl bromoacetate (2.0 ml) at room temperature. The mixture was stirred for 2 hours at the same temperature and partitioned between EtOAc and water. The organic layer was washed with water and brine and evaporated in vacuo. The residue was purified by chromatography on silica gel to give ethyl (R)-{3-{[2-(4,5-diphenyloxazole-2-yl)-1-hydroxy-2-cyclohexen-1-yl]methyl}phenoxy}-acetate (5.3 g).

후처리

  1. washThe mixture was washed with 1N-HCl solution and brine
  2. customevaporated
  3. dissolutionThe residue was dissolved in DMF (50 ml)
  4. additionfollowed by addition of K2CO3 (5 g) and ethyl bromoacetate (2.0 ml) at room temperature
  5. stirringThe mixture was stirred for 2 hours at the same temperature
  6. custompartitioned between EtOAc and water
  7. washThe organic layer was washed with water and brine
  8. customevaporated in vacuo
  9. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-bf2eb6408ae7429d83bed8b74b6077d7
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297267B1

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