Pyridine → (R)-3-[(bromoacetyl)oxy]tetradecanoic acid methyl ester

HRID 37544

反応式

HRID 37544 の反応式
[OH:1][C@H:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[Br:19][CH2:20][C:21](Br)=[O:22].N1C=CC=CC=1>>[CH3:7][O:6][C:4](=[O:5])[CH2:3][C@H:2]([O:1][C:21](=[O:22])[CH2:20][Br:19])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参加物

4

反応物 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 98349453R-hydroxymyristic acid methyl ester

生成物 1

HCID 53830523(R)-3-[(bromoacetyl)oxy]tetradecanoic acid methyl ester収率 90%

実験手順

To a rapidly-stirred slurry of 1.29 g (4.99 mmol) methyl (R)-3-hydroxytetradecanoate and 0.45 ml (5.2 mmol) bromoacetyl bromide in 25 ml hexanes at 0° C. in a flame-dried flask under N2 was added 0.42 ml (5.2 mmol)pyridine all at once. The mixture was removed from the cold bath for 30 min. The mixture was suction filtered through celite, washing with 75 ml ether. The filtrate was washed with 2×100 ml H2O and with 50 ml 10% NaHCO3. The ether was dried over MgSO4 and removed by rotary evaporation, giving 1.70 g (90%) crude (R)-3-[(bromoacetyl)oxy]tetradecanoic acid methyl ester as a yellow oil. Analytically pure samples could be prepared by subjecting the oil to radial chromatography, eluting with CH2Cl2.

後処理

  1. customThe mixture was removed from the cold bath for 30 min
  2. filtrationfiltered through celite
  3. washwashing with 75 ml ether
  4. washThe filtrate was washed with 2×100 ml H2O and with 50 ml 10% NaHCO3
  5. dry with materialThe ether was dried over MgSO4
  6. customremoved by rotary evaporation

出典と根拠

ORDレコード
ord-720c99001e6e47de9d4bb6669ec93d3a
出典データセット
uspto-grants-1995_05
特許番号
US05420305

関連ノート

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