Oxalyl chloride → 8-Fluoro-2,3-dihydro-4H-1-benzopyran-4-one

HRID 600421ノート

反応式

HRID 600421 の反応式
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:19]=[CH:18][CH:17]=[CH:16][C:9]=1[O:10][CH2:11][CH2:12][C:13]([OH:15])=O.[Cl-].[Al+3].[Cl-].[Cl-]>CN(C=O)C.C(Cl)Cl>[F:7][C:8]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:9]=1[O:10][CH2:11][CH2:12][C:13]2=[O:15]

参加物

6

反応物 3

HCID 65578Oxalyl chlorideHCID 15457213-(2-fluorophenoxy)propanoic AcidHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 139538178-Fluoro-2,3-dihydro-4H-1-benzopyran-4-one収率 98%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Oxalyl chloride (8.79 mL) and one drop of DMF were added to an ice cold solution of 3-(2-fluorophenoxy)propanoic acid (9.27 g) in methylene chloride (50 mL). The solution was stirred at 0° C. for two hours, aluminum chloride (7.39 g, 55.42 mM) was added and the solution was stirred for 16 hours at room temperature. The mixture was poured onto ice water, and extracted three times with methylene chloride. The combined organics were washed with 0.5M NaOH and brine, dried, evaporated, and purified by column chromatography (eluting with 20% EtOAc/Hex) to give 8-fluorochroman-4-one (3) (8.20 g, 98%).

後処理

  1. stirringthe solution was stirred for 16 hours at room temperature
  2. additionThe mixture was poured onto ice water
  3. extractionextracted three times with methylene chloride
  4. washThe combined organics were washed with 0.5M NaOH and brine
  5. customdried
  6. customevaporated
  7. custompurified by column chromatography (eluting with 20% EtOAc/Hex)

出典と根拠

ORDレコード
ord-f0e520929165432c8e283d547cb1f46f
出典データセット
uspto-grants-2011_03
特許番号
US07902187B2

反応ノート

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