Methyl iodide → (2SR,9aSR)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7859

반응식

HRID 7859 반응식
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([CH3:19])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:20][CH2:21][O:22][CH3:23])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].[Li+].[CH3:25]C([N-]C(C)C)C.C(=O)=O.CC(C)=O.IC.[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[CH2:1]([C:5]12[CH2:17][CH:16]([CH3:25])[C:15](=[O:18])[C:14]([CH3:19])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:20][CH2:21][O:22][CH3:23])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

참가 물질

8

반응물 5

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 18522661Acetone cardiceHCID 219908939a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

생성물 1

HCID 67401243(2SR,9aSR)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

A solution of 9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (162 mg, 0.52 mmol) in anhydrous THF (2.5 mL) was cooled in an ice bath and stirred under a nitrogen atmosphere while 0.4M LDA in THF (1.55 mL, 0.62 mmol) was added by syringe. After stirring at 0° C. for 30 minutes, the solution was cooled to −78° C. (dry ice-acetone bath) and treated with iodomethane (0.162 mL, 2.6 mmol). The resulting mixture was allowed to slowly warm to room temperature, then stirred at room temperature overnight. The mixture was diluted with EtOAc (60 mL) and shaken with saturated aqueous NH4Cl (40 mL). The aqueous phase was extracted with more EtOAc (20 mL). The combined organics were washed with 5% NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated under vacuum to a yellow oil. The crude product was purified by preparative layer chromatography (PLC) on a 0.1×20×20 cm silica gel GF plate using 4:1 hexanes-EtOAc as developing solvent. The band at Rf 0.44-0.56 was extracted with EtOAc and the extracts evaporated under vacuum to provide (2SR,9aSR)-9a-butyl-2,4-dimethyl-7-methoxymethoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (111 mg) as an oil.

후처리

  1. additionwas added by syringe
  2. temperatureto slowly warm to room temperature
  3. stirringstirred at room temperature overnight
  4. extractionThe aqueous phase was extracted with more EtOAc (20 mL)
  5. washThe combined organics were washed with 5% NaHCO3, water, and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum to a yellow oil
  9. customThe crude product was purified by preparative layer chromatography (PLC) on a 0.1×20×20 cm silica gel GF plate
  10. extractionThe band at Rf 0.44-0.56 was extracted with EtOAc
  11. customthe extracts evaporated under vacuum

출처 및 근거

ORD 기록
ord-95e98eaea1a94f0591c92261b6aa3074
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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