반응식
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.[Li]CCCC.CCCCCC.B(OC)(OC)OC.FC(F)(F)S(O[C:31]1[C:40]2[C:35](=[CH:36][C:37]([CH3:41])=[CH:38][CH:39]=2)[O:34][C:33](=[O:42])[CH:32]=1)(=O)=O>CCOCC.C1COCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:4]1[CH:5]=[CH:6][C:2]([C:31]2[C:40]3[C:35](=[CH:36][C:37]([CH3:41])=[CH:38][CH:39]=3)[O:34][C:33](=[O:42])[CH:32]=2)=[CH:3]1참가 물질
반응물 5
생성물 1
시약·촉매·용매 4
반응 조건
- 온도
- 65 °C
실험 절차
To a solution of 3-bromofuran (2.3 g, 16.1 mmol) in dry Et2O (146 ml) was added at -78° C. n-BuLi in hexane (6.42 ml, 16.1 mmol, 2.5M). The resulting solution was stirred for 20 min, then (MeO)3B (1.82 ml, 16.1 mmol) was added dropwise and after 20 min., a mixture of the triflate from Step 1 (4.50 g, 14.6 mmol) and (PPh3)4Pd (1.69 g, 1.46 mmol) in THF (60 ml) and H2O (10 ml) was added. The cooling bath was removed and the resulting mixture was heated to 65° C. for 1.75 h. The solvent was evaporated and H2O was added followed by extraction with EtOAc (3×50 ml). The combined organic phases were washed with brine, dried over MgSO4 and evaporated. Purification by flash chromatography (toluene:(2-10% EtOAc)) gave 2.5 g of the title compound, m.p. 160°-162° C.
후처리
- additionwas added
- customThe cooling bath was removed
- customThe solvent was evaporated
- additionH2O was added
- extractionfollowed by extraction with EtOAc (3×50 ml)
- washThe combined organic phases were washed with brine
- dry with materialdried over MgSO4
- customevaporated
- customPurification by flash chromatography (toluene:(2-10% EtOAc))
출처 및 근거
- ORD 기록
- ord-e8506f15126a449896a0839e0d8b9da3
- 출처 데이터셋
- uspto-grants-1995_06
- 특허 번호
- US05424320
연결된 노트
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