3-Methyl-2-cyclohexen-1-one → (2R,3R)-7-methyl-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-6-ene

HRID 1423823

반응식

HRID 1423823 반응식
[C:1]1([C@@H:7]([OH:16])[C@@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][C:18]1[CH2:23][CH2:22][CH2:21][C:20](=O)[CH:19]=1>C1C=CC=CC=1.CCOCC.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>[CH3:17][C:18]1[CH2:23][CH2:22][CH2:21][C:20]2([O:9][C@H:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:16]2)[CH:19]=1

참가 물질

6

반응물 2

HCID 145113-Methyl-2-cyclohexen-1-oneHCID 853019(R,R)-Hydrobenzoin

생성물 1

HCID 71116085(2R,3R)-7-methyl-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-6-ene수율 100%

시약·촉매·용매 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)촉매HCID 241Benzene용매2회HCID 3283Diethyl Ether용매

반응 조건

온도
115 °C

실험 절차

(1R,2R)-1,2-diphenyl-1,2-ethanediol (150 g, 699 mmol) and 3-methyl-2-cyclohexen-1-one (77 g, 699 mmol) were suspended in benzene (1398 mL) and treated with PPTS (4.39 g, 17.48 mmol). The flask was fitted with a Dean-Stark trap filled with benzene and a condenser. The reaction was heated to 115° C. for 3 days, and then the reaction was cooled to ambient temperature and diluted with ether. The mixture was washed with saturated aq NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated to give a red/orange liquid (214 g, 100% yield). The liquid was used without further purification.

후처리

  1. customThe flask was fitted with a Dean-Stark trap
  2. temperaturethe reaction was cooled to ambient temperature
  3. washThe mixture was washed with saturated aq NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-27725d2cfd664a99bd9a90878c8a8163
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927585B2

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