Propanal → 2-(2-Oxobutyl)-4-hydroxy-1-indanone

HRID 974781ノート

反応式

HRID 974781 の反応式
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH:12](=[O:15])[CH2:13][CH3:14].C(N([CH2:21][CH3:22])CC)C.[CH2:23]([OH:25])[CH3:24]>[I-].C[N+]1C(C)=C(CCO)SC=1.C(Cl)Cl>[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[CH2:12])[C:8]2=[O:11])=[CH:4][CH:3]=1.[O:15]=[C:12]([CH2:21][CH3:22])[CH2:13][CH:14]1[CH2:2][C:10]2[C:9](=[CH:5][CH:4]=[CH:24][C:23]=2[OH:25])[C:8]1=[O:11]

参加物

8

反応物 4

HCID 527PropanalHCID 702EthanolHCID 8471TriethylamineHCID 70206596-Hydroxy-1-indanone

生成物 2

HCID 199694252-(2-Oxobutyl)-4-hydroxy-1-indanone収率 70%HCID 199694276-Hydroxy-2-methylene-1-indanone

試薬・触媒・溶媒 2

HCID 98387703,4-Dimethyl-5-(2-hydroxyethyl)thiazolium iodide触媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

6-Hydroxy-2-methylene-1-indanone was prepared using a similar method to that described in Example 16 but using 6-hydroxy-1-indanone instead of 4-hydroxy-1-indanone. To the above compound (0.3 g; 1.87 mmol) in suspension in ethanol, were added, at ambient temperature, under argon: propionaldehyde (0.27 ml; 3.75 mmol), triethylamine (80 μl; 0.56 mmol) and 3,4-dimethyl-5-(2hydroxyethyl)thiazolium iodide (50.6 mg; 0.18 mmol). The mixture was heated at 80° C. for 17 hours. The solution was taken up in CH2Cl2 and washed in water and a saturated solution of NaCl. The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (7/3), to give 2-(2-oxobutyl)-4-hydroxy-1-indanone (0.28 g; 70%).

後処理

  1. washwashed in water
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with petroleum ether/ethyl acetate (7/3)

出典と根拠

ORDレコード
ord-7cb3c88aa8c04ff1a59864567197c248
出典データセット
uspto-grants-1997_03
特許番号
US05607928

反応ノート

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