Sulfuric Acid → 4-Hydroxy-2'-nitrobutyrophenone

HRID 342189ノート

反応式

HRID 342189 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[C:11][CH2:12][CH2:13][OH:14])([O-:3])=[O:2].[OH:15]S(O)(=O)=O>O1CCCC1.O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:15])[CH2:11][CH2:12][CH2:13][OH:14])([O-:3])=[O:2]

参加物

5

反応物 2

HCID 1118Sulfuric Acid2 回HCID 117454514-(2-Nitrophenyl)but-3-yn-1-ol

生成物 1

HCID 109767084-Hydroxy-2'-nitrobutyrophenone収率 37%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

A mixture of HgO (0.21 g, 1.0 mmol) in 50 ml of 0.12N H2SO4 is heated to 60° C., treated dropwise with a solution of 4-(o-nitrophenyl)-3-butyne-1-ol (3.70 g, 19.4 mmol) in 25 ml of tetrahydrofuran over a 10 minute period, held at 60° C. for 3 hours, treated with additional HgO (0.84 g, 3.9 mmol) suspended in 25 ml of 0.12N H2SO4, held at 60° C. for 4 hours, cooled to room temperature and diluted with water. The resultant aqueous mixture is extracted with ether. The extracts are combined, washed with brine, dried over Na2SO4 and concentrated in vacuo to give a residue. The residue is purified by flash column chromatography (silica gel; gradient 1:1→2:1 ethyl acetate: hexanes as eluent) to give the title product as a brown oil, 1.48 g, 37% yield, identified by NMR and mass spectral analyses.

後処理

  1. additiontreated with additional HgO (0.84 g, 3.9 mmol)
  2. waitheld at 60° C. for 4 hours
  3. temperaturecooled to room temperature
  4. extractionThe resultant aqueous mixture is extracted with ether
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give a residue
  9. customThe residue is purified by flash column chromatography (silica gel; gradient 1:1→2:1 ethyl acetate: hexanes as eluent)

出典と根拠

ORDレコード
ord-00c644a877304e7c9b86507b26f1e67f
出典データセット
uspto-grants-1999_01
特許番号
US05856576

反応ノート

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