Hydrochloric Acid → 1-Hydroxy-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclopentane

HRID 377301노트

반응식

HRID 377301 반응식
[C:1]1([C:7]2[N:8]=[CH:9][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.C([Li])CCC.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:35]=[CH:36][CH:37]=1)[CH2:28][CH:29]1[CH2:33][CH2:32][CH2:31][C:30]1=[O:34].Cl>O1CCCC1.C(OCC)(=O)C>[OH:34][C:30]1([C:9]2[O:10][C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[CH2:31][CH2:32][CH2:33][CH:29]1[CH2:28][C:27]1[CH:35]=[CH:36][CH:37]=[C:25]([O:24][CH3:23])[CH:26]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6134984,5-DiphenyloxazoleHCID 114242592-(3-Methoxybenzyl)cyclopentanoneHCID 178418339Butyllithium

생성물 1

HCID 193585111-Hydroxy-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclopentane

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

To a solution of 4,5-diphenyloxazole in tetrahydrofuran (100 ml) at -78° C. under nitrogen was added n-butyllithium (in hexane, 1,7N, 12 ml). After 30 minutes, at the same temperature a solution of 2-(3-methoxybenzyl)cyclopentanone (3.8 g) in tetrahydrofuran (10 ml) was added dropwise thereto. After being stirred for 1 hour at 0° C., the reaction mixture was poured into a mixture of ethyl acetate (200 ml) and 1N-hydrochloric acid (50 ml). The organic layer was washed with saturated sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was chromatographed (n-hexane--ethyl acetate:5:1-2:1) on silica gel to afford 1-hydroxy-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclopentane (8.0 g).

후처리

  1. washThe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe oily residue was chromatographed (n-hexane--ethyl acetate:5:1-2:1) on silica gel

출처 및 근거

ORD 기록
ord-ba5a9907b0fd41f2aa07702cd82f2860
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06025375

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