Ammonium Chloride → 5-[(4S,5R)-4,6-diacetoxy-1-hydroxy-5-(1-methoxy-1-methylethyloxy)-2-hexen-1-yl]-4-octyl-4-trimethylsilyloxy-2-cyclopentenone

HRID 1886228노트

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HRID 1886228 반응식
[CH2:1]([C:9]1([O:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH2:13][C:12](=[O:14])[CH:11]=[CH:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(C(C)C)CC)(C)C.O1C=CC=C1C([O-])=O.O1C=CC=C1C([O-])=O.O1C=CC=C1C([O-])=O.C([B+3]CCCC)CCC.[C:62]([O:65][C@H:66]([C@H:71]([O:77][C:78]([O:81][CH3:82])([CH3:80])[CH3:79])[CH2:72][O:73][C:74](=[O:76])[CH3:75])[CH:67]=[CH:68][CH:69]=[O:70])(=[O:64])[CH3:63].[Cl-].[NH4+]>CCOCC.CCCCCC>[C:62]([O:65][C@H:66]([C@H:71]([O:77][C:78]([O:81][CH3:82])([CH3:80])[CH3:79])[CH2:72][O:73][C:74](=[O:76])[CH3:75])[CH:67]=[CH:68][CH:69]([CH:13]1[C:12](=[O:14])[CH:11]=[CH:10][C:9]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[O:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[OH:70])(=[O:64])[CH3:63]

참가 물질

8

반응물 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 137677604-Octyl-4-trimethylsilyloxy-2-cyclopentenoneHCID 57122051(4S,5R)-4,6-diacetoxy-5-(1-methoxy-1-methylethyloxy)-2-hexenalHCID 178440533HCID 178440533, 화합물

생성물 1

HCID 678636745-[(4S,5R)-4,6-diacetoxy-1-hydroxy-5-(1-methoxy-1-methylethyloxy)-2-hexen-1-yl]-4-octyl-4-trimethylsilyloxy-2-cyclopentenone수율 59.7%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

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온도
-78 °C

실험 절차

A solution composed of 1 g (3.55 mmoles) of 4-octyl-4-trimethylsilyloxy-2-cyclopentenone, 5 ml of dry hexane and 5 ml of dry ether was cooled to -78° C. under a nitrogen stream, and 870 microliters (5 mmoles) of diisopropylethylamine and then 4.6 ml (4.6 mmoles) of dibutylboron trifurate (lM CH2Cl2 solution) were added. The mixture was stirred at -78° C. for 1 hour. An ether solution (3 ml) of 1070 mg (3.55 mmoles) of (4S,5R)-4,6-diacetoxy-5-(1-methoxy-1-methylethyloxy)-2-hexenal was added, and the mixture was stirred for 2 hours. After the reaction, an aqueous solution of ammonium chloride was added to terminate the reaction, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous potassium hydrogen sulfate solution, an aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution in this sequence, and dried over anhydrous magnesium sulfate solution. The solvent was evaporated under reduced pressure, and the resulting oily product was subjected to Florisil column chromatography (hexane:ethyl acetate: 5:1→3:1) to give 1.24 g (59%) of an aldol product.

후처리

  1. stirringthe mixture was stirred for 2 hours
  2. customAfter the reaction
  3. customto terminate
  4. customthe reaction
  5. extractionthe reaction mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with an aqueous potassium hydrogen sulfate solution
  7. dry with materialan aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution in this sequence, and dried over anhydrous magnesium sulfate solution
  8. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-15c5bf96cbd4451b8202bfd0767bf77a
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05149711

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