Triphenylphosphine → Methyl (3-(2-bromoethyl)benzofuran-7-yloxy)acetate

HRID 430749노트

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HRID 430749 반응식
O[CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:7]=2[O:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:38]N1C(=O)CCC1=O>CCCCCC>[Br:38][CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:7]=2[O:6][CH:5]=1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 11230436Methyl (3-(2-hydroxyethyl)benzofuran-7-yloxy)acetate

생성물 1

HCID 20708443Methyl (3-(2-bromoethyl)benzofuran-7-yloxy)acetate수율 85.4%

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
0 °C

실험 절차

Methyl (3-(2-hydroxyethyl)benzofuran-7-yloxy)acetate (1.30 g) was dissolved in THE (15 ml) and the solution was cooled to 0° C. To this solution, triphenylphosphine (2.05 g) and N-bromosuccinimide (NBS, 1.39 g) were added and the resulting solution was stirred for 1 hour. Hexane (10 ml) was added to the reaction solution and the reaction solution was filtered through Celite. The filtrate was poured into water layer (50 ml) and extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated brine, followed by drying the resultant over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1) using silica gel to obtain the desired compound (1.39 g, yield: 85%).

후처리

  1. filtrationthe reaction solution was filtered through Celite
  2. additionThe filtrate was poured into water layer (50 ml)
  3. extractionextracted twice with ethyl acetate (20 ml)
  4. washwashed with saturated brine
  5. dry with materialby drying the resultant over sodium sulfate
  6. customAfter removing the sodium sulfate
  7. filtrationby filtration
  8. customthe solvent was removed under reduced pressure
  9. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1)

출처 및 근거

ORD 기록
ord-abda48a5cade4c6fbc87a44b6168d1e8
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323235B1

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