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

HRID 430749ノート

反応式

HRID 430749 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-abda48a5cade4c6fbc87a44b6168d1e8
出典データセット
uspto-grants-2001_11
特許番号
US06323235B1

反応ノート

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