Boron tribromide → 9a-BUTYL-7-HYDROXY-8-METHYL-1,2,9,9a-TETRAHYDRO-3H-FLUOREN-3-ONE

HRID 7849

반응식

HRID 7849 반응식
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[CH:14]=[C:13]1[C:12]1[C:7](=[C:8]([CH3:21])[C:9]([O:19]C)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[CH:14]=[C:13]1[C:12]1[C:7](=[C:8]([CH3:21])[C:9]([OH:19])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 219908849a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

생성물 1

HCID 99652729a-BUTYL-7-HYDROXY-8-METHYL-1,2,9,9a-TETRAHYDRO-3H-FLUOREN-3-ONE수율 99.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 9a-butyl-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (28.4 mg, 0.1 mmol) in anhydrous CH2Cl2 (1.7 mL) was stirred under a nitrogen atmosphere and cooled in a dry ice-acetone bath while 1M BBr3 in CH2Cl2 (0.30 mL, 0.3 mmol) was added dropwise by syringe. The cooling bath was removed and the reaction mixture was stirred at room temperature for 4 hours. The mixture was diluted with EtOAc (8 mL), water (3 mL) and 1N HCL (1 mL) and shaken vigorously. The EtOAc layer was separated, washed with water (3 mL), 1M pH 3 phosphate (3 mL) and brine (3 mL), dried over MgSO4, filtered and evaporated under vacuum to give an ochre solid (26.8 mg). The crude product was suspended in CDCl3 (1 mL) and filtered. The solid portion was dried under vacuum to afford 9a-butyl-7-hydroxy-8-methyl-1,2,9,9a-3H-tetrahydro-fluoren-3-one as an olive colored powder.

후처리

  1. additionwas added dropwise by syringe
  2. customThe cooling bath was removed
  3. additionThe mixture was diluted with EtOAc (8 mL), water (3 mL) and 1N HCL (1 mL)
  4. stirringshaken vigorously
  5. customThe EtOAc layer was separated
  6. washwashed with water (3 mL), 1M pH 3 phosphate (3 mL) and brine (3 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-a3003665ff944b9aba117505583cfbac
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087599B2

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