Trifluoroacetic acid → 7-hydroxy-4-methyl-2H-chromene-3-carbaldehyde

HRID 217459

反応式

HRID 217459 の反応式
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([CH3:21])=[C:14]([CH:19]=[O:20])[CH2:15][O:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CC1C=C(C)C(C)=C(C)C=1C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([CH3:21])=[C:14]([CH:19]=[O:20])[CH2:15][O:16]2)=[CH:11][CH:10]=1

参加物

5

反応物 4

HCID 6422Trifluoroacetic acidHCID 12784PentamethylbenzeneHCID 516892Sodium BicarbonateHCID 58438777HCID 58438777、化合物

生成物 1

HCID 584391347-hydroxy-4-methyl-2H-chromene-3-carbaldehyde収率 83.3%

実験手順

To 7-(benzyloxy)-4-methyl-2H-chromene-3-carbaldehyde (230 mg) and 1,2,3,4,5-pentamethylbenzene (608 mg) was added TFA (3 mL), followed by stirring at room temperature overnight. The reaction liquid was poured into an aqueous NaHCO3 solution, followed by extraction with EtOAc three times. The organic layer was combined, washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=80:20 to 20:80) to obtain 7-hydroxy-4-methyl-2H-chromene-3-carbaldehyde (130 mg) as a pale yellow powder.

後処理

  1. customThe reaction liquid
  2. extractionfollowed by extraction with EtOAc three times
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=80:20 to 20:80)

出典と根拠

ORDレコード
ord-4ebbd41767474eba8cde355d40fd4ffc
出典データセット
uspto-grants-2012_06
特許番号
US08193378B2

関連ノート

読み込み中…