Ethyl benzoylacetate → Ethyl 3-phenylhydracrylate, (+-)-

HRID 1649712ノート

反応式

HRID 1649712 の反応式
[C:1]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C>[C:2]1([CH:1]([OH:8])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

3

反応物 1

HCID 7170Ethyl benzoylacetate

生成物 1

HCID 99818Ethyl 3-phenylhydracrylate, (+-)-収率 99%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Ethyl benzoylacetate (1) (19.21 g; 0.10 mol) was dissolved in 95% ethanol (100 mL) in a pressure bottle. The bottle was purged with nitrogen and 5% palladium on carbon (960 mg; 5 weight %) was added. The vessel was placed under 45 psi H2 and shaken on a Parr apparatus for 14 hours, at which time H2 uptake had halted and thin layer chromatographic analysis indicated (1) was present. The reaction mixture was suction-filtered through Celite with a top sand layer (to prevent channels) and eluted with ether to remove the catalyst. The filtrate was concentrated to afford (2), racemic ethyl 3-phenyl-3-hydroxypropionate (19.17 g; 99%) which was pure by tlc and 1H nmr analysis. 1H nmr (300 MHz, CDCl3): 7.4-7.2 (5H, m); 5.130(1H,dd,J=4.36, 8.48 Hz); 4.178 (2H, q, J=7.17 Hz); 3.2(1H, br s); 2 764(1H, dd, J=8.58, 16.30 Hz); 2.691 (1H, dd, J=4.33, 16.33 Hz); 1.259(3H, t, J=7.17 Hz). IR (neat film, cm-1) 3450 (s,b); 1720(s); 1605(w). EIMS (m/e): 194 (M+); 165 (2%, M+ - Et); 149 (5%, M+ -EtO).

後処理

  1. customThe bottle was purged with nitrogen and 5% palladium on carbon (960 mg; 5 weight %)
  2. additionwas added
  3. filtrationThe reaction mixture was suction-filtered through Celite with a top sand layer (to prevent channels)
  4. washeluted with ether
  5. customto remove the catalyst
  6. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-b2abd56290e74857a257765e54bc39d3
出典データセット
uspto-grants-1990_05
特許番号
US04921798

反応ノート

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