Sodium Hydroxide → 9a-[(1E)-1-butenyl]-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7829

반응식

HRID 7829 반응식
[CH:1](/[C:5]1([CH2:17][CH2:18][C:19](=[O:22])[CH2:20][CH3:21])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=O)=[CH:2]\[CH2:3][CH3:4].[OH-].[Na+]>CO>[CH:1](/[C:5]12[CH2:17][CH2:18][C:19](=[O:22])[C:20]([CH3:21])=[C:6]1[C:7]1[C:12](=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=1)[CH2:13]2)=[CH:2]\[CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 219908822-[(1E)-1-butenyl]-5-methoxy-2-(3-oxopentyl)-1-indanone

생성물 1

HCID 219908999a-[(1E)-1-butenyl]-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one수율 35.8%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
85 °C

실험 절차

A solution of 2-[(1E)-1-butenyl]-5-methoxy-2-(3-oxopentyl)-1-indanone (199 mg, 0.663 mmol) in methanol (5 mL) was treated with 2N aqueous NaOH (1.6 mL) and the resulting mixture was stirred and heated in an oil bath at 85° C. for 7 hours. After cooling to room temperature, the brown solution was partitioned between EtOAc (20 mL) and 0.4N HCl (10 mL). The organic phase was separated, washed with brine (15 ml), dried over MgSO4, filtered, and evaporated under vacuum to a brown oil (208 mg). The crude product was purified by silica gel chromatography on a Biotage FLASH 12S column (1.2×7.5 cm), eluting with 5:1 hexanes:EtOAc, to afford 9a-[(1E)-1-butenyl]-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (67 mg) as an oil.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe brown solution was partitioned between EtOAc (20 mL) and 0.4N HCl (10 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (15 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum to a brown oil (208 mg)
  8. customThe crude product was purified by silica gel chromatography on a Biotage FLASH 12S column (1.2×7.5 cm)
  9. washeluting with 5:1 hexanes

출처 및 근거

ORD 기록
ord-0caa973e2b6a45ab9fd8c25a7a357edd
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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