Methanol → 5,6-Dibromo-4,7-dimethyl-1,4-epoxy-1,4-dihydronaphthalene

HRID 28789

반응식

HRID 28789 반응식
Br[C:2]1[C:7]([CH3:8])=[C:6]([Br:9])[C:5]([Br:10])=[C:4]([CH3:11])[C:3]=1Br.[O:13]1C=[CH:16][CH:15]=[CH:14]1.[Li][CH2:19]CCC.CO>C1(C)C=CC=CC=1.O>[Br:10][C:5]1[C:6]([Br:9])=[C:7]([CH3:8])[CH:2]=[C:3]2[C:4]=1[C:11]1([CH3:19])[O:13][CH:14]2[CH:15]=[CH:16]1

참가 물질

7

반응물 4

HCID 887MethanolHCID 8029FuranHCID 31952Benzene, 1,2,4,5-tetrabromo-3,6-dimethyl-HCID 178418339Butyllithium

생성물 1

HCID 226789125,6-Dibromo-4,7-dimethyl-1,4-epoxy-1,4-dihydronaphthalene수율 50%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
-78 °C

실험 절차

To tetrabromo para-xylene (2.1 g, 5.0 mmol) and furan (4 g, 58.8 mmol) in PhMe (55 mL) at −78° C. was added BuLi (2.2 mL, 2.5M in hexanes, 5.5 mmol) dropwise. The reaction was stirred for two hours at −78° C. and the allowed to warm to rt. After 3 hours, MeOH (2 mL) was added and the reaction mixture was poured into water. The organic layer was separated and the aqueous layer was extracted three times with Et2O. The combined organic layers were washed with brine, dried over MgSO4, and concentrated. Flash chromatography on silca gel gave 26 (185 mg, 50%) as a white solid. The spectral data correlates well with the literature values. 22

후처리

  1. temperatureto warm to rt
  2. waitAfter 3 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted three times with Et2O
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d83172b32ece455e8c15e3a664faf33b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420003B2

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