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Hexane → 4-(3-Furyl)-7-methylcoumarin

HRID 21563
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HRID 21563 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]1
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참가 물질

10

반응물 5

HCID 8058HexaneHCID 8470Trimethyl borateHCID 891643-BromofuranHCID 233702387-Methyl-2-oxo-2H-chromen-4-YL trifluoromethanesulfonateHCID 178418339Butyllithium

생성물 1

HCID 233701904-(3-Furyl)-7-methylcoumarin수율 75.7%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매
HCID 962Water용매
HCID 3283Diethyl Ether용매
HCID 8028Tetrahydrofuran용매

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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

  1. additionwas added
  2. customThe cooling bath was removed
  3. customThe solvent was evaporated
  4. additionH2O was added
  5. extractionfollowed by extraction with EtOAc (3×50 ml)
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customPurification by flash chromatography (toluene:(2-10% EtOAc))

출처 및 근거

ORD 기록
ord-e8506f15126a449896a0839e0d8b9da3
출처 데이터셋
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05424320

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