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

HRID 974781노트

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HRID 974781 반응식
[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]

참가 물질

8

반응물 4

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

생성물 2

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

시약·촉매·용매 2

HCID 98387703,4-Dimethyl-5-(2-hydroxyethyl)thiazolium iodide촉매HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-7cb3c88aa8c04ff1a59864567197c248
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05607928

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