Acetic Anhydride → HCID 14178171、化合物

HRID 1789222ノート

反応式

HRID 1789222 の反応式
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH:6]([OH:14])[C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=1)[CH3:2].[C:16](OC(=O)C)(=[O:18])[CH3:17]>C(OCC)(=O)C.CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH:6]([O:14][C:16](=[O:18])[CH3:17])[C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=1)[CH3:2]

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 14178170Ethyl 3-Hydroxy-3-(6-methyl-3-pyridyl)propanoate

生成物 1

HCID 14178171HCID 14178171、化合物収率 100.9%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

45.9 g (0.22 mol) of 3-hydroxy-3-(2-methyl-5-pyridyl)-propionic acid ethyl ester was dissolved in 100 ml of ethyl acetate, and 50 ml (0.53 mol) of acetic anhydride and 0.1 g (0.82 mmol) of 4-dimethylaminopyridine were added. The solution was stirred for 6 hours at 20° C. and then evaporated. The residue was dissolved in 50 ml methylene chloride and 50 ml of 5 percent sodium hydroxide solution, the phases were separated and the organic phase was evaporated. 55.8 g of raw 3-acetoxy-3-(2-methyl-5-pyridyl)-propionic acid ethyl ester was obtained. This raw product was dissolved in 300 ml of acetic acid with 3.0 g of 5 percent palladium on carbon and fed into a 1-liter autoclave. The autoclave was put under 8 bars of hydrogen and stirred at 70° C. Hydrogenation was ended after 6 hours. The autoclave was cooled and opened, and the solution was filtered and evaporated. The residue was dissolved in 50 ml of water and brought to pH 8 by potassium carbonate. The solution was extracted three times with 100 ml of methylene chloride and the organic extracts were evaporated. 42.5 g of raw 2-methyl- pyridine-5-propionic acid ethyl ester was obtained. The raw product was distilled (b.p. 100°-110° C./1.0 mbar). 22.0 g of 2-methylpyridine-5-propionic acid ethyl ester was obtained, with a GC content of 92 percent. The yield, in relation to the 6-methyl nicotinoyl propionic acid ethyl ester, was 62.9 percent.

後処理

  1. customevaporated
  2. dissolutionThe residue was dissolved in 50 ml methylene chloride
  3. custom50 ml of 5 percent sodium hydroxide solution, the phases were separated
  4. customthe organic phase was evaporated

出典と根拠

ORDレコード
ord-eb4ae90a1b0b41d0abcdfe869a7b004c
出典データセット
uspto-grants-1987_08
特許番号
US04687856

反応ノート

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