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Methanesulfonic Acid → 6-Fluoro-1-benzopyran-2-carboxylic acid methyl ester

HRID 875253
ノート
印刷プレビュー

反応式

HRID 875253 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][C:7](=O)[C:6]=2[CH:15]=1.[H][H].[CH3:18]S(O)(=O)=O>C1COCC1.[Pd]>[CH3:18][O:13][C:11]([CH:9]1[CH:8]=[CH:7][C:6]2[CH:15]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:10]1)=[O:12]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6395Methanesulfonic AcidHCID 40960466-fluoro-4-oxo-4H-chromene-2-carboxylic acidHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 673938016-Fluoro-1-benzopyran-2-carboxylic acid methyl ester収率 480.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
22.5 °C

実験手順

20 g of 6-fluoro-4-oxo-4H-1-benzopyran-2-carboxylic acid (96 mmol) were hydrogenated under 4 bars of hydrogen in 200 ml THF with 2 g of methanesulfonic acid (20 mmol) and 2 g of 5% Pd on charcoal (Type Escat 112, Engelhard) at 45-55° C. until consumption of hydrogen was no longer observed. The reaction progress was monitored by TLC. The catalyst was then removed by filtration and the reaction mixture concentrated to 40 ml under reduced pressure. 100 ml of methanol were then added and the mixture (solution) was stirred at 20-25° C. until less than 1% of 6-fluoro-3,4-dihydro-2H-chromen-2-carboxylic acid was detected (TLC). The solution was then concentrated under reduced pressure and the residue was dissolved in 60 ml of THF then concentrated under reduced pressure to remove water by azeotropic distillation to give 20 g of the title compound (yield: 100%).

後処理

  1. customThe catalyst was then removed by filtration
  2. concentrationthe reaction mixture concentrated to 40 ml under reduced pressure
  3. addition100 ml of methanol were then added
  4. concentrationThe solution was then concentrated under reduced pressure
  5. dissolutionthe residue was dissolved in 60 ml of THF
  6. concentrationthen concentrated under reduced pressure
  7. customto remove water
  8. distillationby azeotropic distillation

出典と根拠

ORDレコード
ord-eca4c2cc50104622bfed2f5d2d9e7a83
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08981127B2

反応ノート

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