Ammonium Chloride → 4-Butyl-2-chloro-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-trimethylsilyloxy-2-cyclopentenone

HRID 986331노트

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HRID 986331 반응식
[CH2:1]([C:5]1([O:12][Si:13]([C:16](C)(C)C)([CH3:15])[CH3:14])[CH2:9][C:8](=[O:10])[C:7]([Cl:11])=[CH:6]1)[CH2:2][CH2:3][CH3:4].C([N-]C(C)C)(C)C.[Li+].[O:28]=[CH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([C:5]1([O:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[CH:9]([CH:29]([OH:28])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])[C:8](=[O:10])[C:7]([Cl:11])=[CH:6]1)[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 3015770Methyl 7-oxoheptanoateHCID 201584314-Butyl-4-t-butyldimethylsilyloxy-2-chloro-2-cyclopentenone

생성물 1

HCID 201583884-Butyl-2-chloro-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-trimethylsilyloxy-2-cyclopentenone수율 33%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

54 mg of 4-butyl-4-t-butyldimethylsilyloxy-2-chloro-2-cyclopentenone was dissolved in 2 ml of dry tetrahydrofuran, and the solution was cooled to -78° C. With stirring, a lithium diisopropyl amide solution was added. At -78° C., the mixture was stirred for 30 minutes. A solution of 50 mg of methyl 7-oxoheptanoate in 1 ml of dry tetrahydrofuran was added, and the mixed solution was stirred at -78° C. to -50° C. for 1 hour. A saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was chromatographed on a silica gel column (silica gel 30 g; hexane:ethyl acetate=50:1→10:1) to give 29 mg (yield 33%) of a low polarity isomer of 4-butyl-2-chloro-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-trimethylsilyloxy-2-cyclopentenone and 17 mg (yield 20%) of its high polarity isomer.

후처리

  1. stirringAt -78° C., the mixture was stirred for 30 minutes
  2. stirringthe mixed solution was stirred at -78° C. to -50° C. for 1 hour
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration and concentration
  7. customthe residue was chromatographed on a silica gel column (silica gel 30 g; hexane:ethyl acetate=50:1→10:1)

출처 및 근거

ORD 기록
ord-df65adf487904ead973e61d3c06b8c6c
출처 데이터셋
uspto-grants-1987_12
특허 번호
US04711895

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