Acetic Acid → 9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7879

반응식

HRID 7879 반응식
C(C1CC2C(=CC=C(OC)C=2Cl)C1=O)CCC.C(C(C)=O)=C.C[O-].[Na+].CO.[CH2:28]([C:32]1([CH2:45][CH2:46][C:47](=[O:49])[CH3:48])[CH2:40][C:39]2[C:34](=[CH:35][CH:36]=[C:37]([O:42][CH3:43])[C:38]=2[Cl:41])[C:33]1=O)[CH2:29][CH2:30][CH3:31].N1CCCC1.C(O)(=O)C>O1CCCC1.C1(C)C=CC=CC=1>[CH2:28]([C:32]12[CH2:45][CH2:46][C:47](=[O:49])[CH:48]=[C:33]1[C:34]1[C:39](=[C:38]([Cl:41])[C:37]([O:42][CH3:43])=[CH:36][CH:35]=1)[CH2:40]2)[CH2:29][CH2:30][CH3:31]

참가 물질

10

반응물 7

HCID 176Acetic AcidHCID 887MethanolHCID 6570Methyl vinyl ketoneHCID 31268PyrrolidineHCID 10942334Sodium MethoxideHCID 219909122-Butyl-4-chloro-5-methoxy-2-(3-oxobutyl)-1-indanoneHCID 219909172-Butyl-4-chloro-5-methoxy-1-indanone

생성물 1

HCID 219909239a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution 2-butyl-4-chloro-5-methoxy-1-indanone (550 mg, 2.03 mmol) in tetrahydrofuran (4.06 mL) was treated with methyl vinyl ketone (0.203 mL, 2.44 mmol) and 0.5N sodium methoxide in methanol (0.812 mL, 0.406 mmol). The mixture was stirred at room temperature for 90 minutes to effect conversion to 2-butyl-4-chloro-5-methoxy-2-(3-oxobutyl)-1-indanone. The reaction mixture was evaporated under vacuum. The residue in toluene (10 mL) was treated with pyrrolidine (0.170 mL, 2.03 mmol) and acetic acid (0.140 mmol, 2.44 mmol). The resulting mixture was stirred and heated in an oil bath at 80° C. for 2.5 hours. After cooling to room temperature, the mixture was partitioned between EtOAc and water. The organic phase was washed with 0.1N HCl, saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by preparative layer chromatography on silica gel GF plates to afford 9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one.

후처리

  1. customThe reaction mixture was evaporated under vacuum
  2. stirringThe resulting mixture was stirred
  3. temperatureheated in an oil bath at 80° C. for 2.5 hours
  4. temperatureAfter cooling to room temperature
  5. customthe mixture was partitioned between EtOAc and water
  6. washThe organic phase was washed with 0.1N HCl, saturated aqueous NaHCO3 and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under vacuum
  10. customThe residue was purified by preparative layer chromatography on silica gel GF plates

출처 및 근거

ORD 기록
ord-5089406476cf406e8260118814d5a2c0
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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