Trifluoroacetic acid → 5,6-Difluoro-2,3-dihydro-1H-isoindol-1-one

HRID 877232ノート

反応式

HRID 877232 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[C:7](=O)[NH:6][CH:5]2[OH:13].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[F:11][C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[F:1])[C:5](=[O:13])[NH:6][CH2:7]2

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 581363585,6-Difluoro-3-hydroxy-2,3-dihydro-1H-isoindol-1-one

生成物 1

HCID 213653915,6-Difluoro-2,3-dihydro-1H-isoindol-1-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

748 mg of 5,6-difluoro-3-hydroxy-2,3-dihydro-1H-isoindol-1-one (crude product, about 4.04 mmol) were initially charged in 50 ml of dichloromethane, 3.8 ml (48.5 mmol) of trifluoroacetic acid and 1.3 ml (8.08 mmol) of triethylsilane were added and the mixture was stirred overnight at RT. The reaction mixture was then concentrated, and the residue was dissolved in dichloromethane and washed with sodium bicarbonate solution. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 1:1 to 0:1). This gave 72 mg (10.6% of theory) of the target compound.

後処理

  1. concentrationThe reaction mixture was then concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with sodium bicarbonate solution
  4. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 1:1 to 0:1)

出典と根拠

ORDレコード
ord-f0faaf2f2896460b90cb995aae3a7162
出典データセット
uspto-grants-2015_03
特許番号
US08987256B2

反応ノート

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