Sodium Carbonate → HCID 57572363、化合物

HRID 907517ノート

反応式

HRID 907517 の反応式
[CH:1]1([C:6]2[CH2:10][CH2:9][C:8](=[N:11][OH:12])[C:7]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.CCCCCC>[CH:1]1([C:6]2[CH2:10][CH2:9][C:8](=[N:11][OH:12])[C:7]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 73064693HCID 73064693、化合物

生成物 1

HCID 57572363HCID 57572363、化合物収率 46.9%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

To a stirred solution of 27 mg 3-cyclopentyl-2-(3-methoxyphenyl)-2-cyclopenten-1-one oxime (Example 7) in 5 ml dichloromethane at −78° C., was added 0.5 ml 1.0 M boron tribromide in hexane dropwise under inert atmosphere. The reaction mixture was stirred for 2 hours while being allowed to gradually warm to room temperature. Then the reaction mixture was poured into saturated aqueous sodium carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography (silica gel, hexane/ethyl acetate=1:1) to yield 12 mg of 3-cyclopentyl-2-(3-hydroxyphenyl)-2-cyclopenten-1-one oxime as a solid. mp=207-209° C.; 1H NMR (CDCl3, 300 MHz): δ 7.26-7.21 (m, 2H), 6.79-6.70 (m, 3H), 2.93 (m, 1H), 2.80 (m, 2H), 2.61 (m, 2H), 1.70 (m, 4H), 1.54 (m, 4H); APCI MS: m/z 258.1 (M+1).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by column chromatography (silica gel, hexane/ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-ff4b4ee53eb846d9bfc5a5129415d679
出典データセット
uspto-grants-2011_09
特許番号
US08013187B2

反応ノート

読み込み中…