Ethyl Lactate → Ethyl 2-benzyloxylactate

HRID 1271797ノート

反応式

HRID 1271797 の反応式
FC(F)(F)S(O)(=O)=[O:4].[C:9]([O:14][CH2:15][CH3:16])(=[O:13])[CH:10]([CH3:12])[OH:11].ClC(Cl)(Cl)C(=N)O[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1CCCCC1>ClCCl>[CH2:21]([O:11][C:10]([CH3:12])([OH:4])[C:9]([O:14][CH2:15][CH3:16])=[O:13])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 4

HCID 7344Ethyl LactateHCID 8078CyclohexaneHCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidate

生成物 1

HCID 18454908Ethyl 2-benzyloxylactate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoromethanesulfonic acid (1.0 mL) was added gradually to a stirred mixture of ethyl lactate (8.90 g, 75 mmole), benzyl 2,2,2-trichloroacetimidate (22.7 g, 90 mmole), anhydrous cyclohexane (100 mL), and anhydrous dichloromethane (50 mL). The mixture was stirred overnight at room temperature under argon atmosphere. The mixture was filtered, and the filtrate was washed with saturated solution of sodium hydrogen carbonate (250 mL), and with distilled water (250 mL). Then, the solution was dried with anhydrous sodium sulfate and the solvents were distilled under reduced pressure using a rotary evaporator. The residue was subjected to fractional vacuum distillation giving 9.6 g of colorless product. NMR (CDCl3): 1.21 ppm (t, —CH2CH3, 3H), 1.32 ppm (d, —CH2—, 3H), 4.13 ppm (m, —CH— and —CH2CH3, 3H), 4.50 ppm (m, —CH2—, 2H), 7.32 ppm (m, 5H).

後処理

  1. filtrationThe mixture was filtered
  2. washthe filtrate was washed with saturated solution of sodium hydrogen carbonate (250 mL)
  3. dry with materialThen, the solution was dried with anhydrous sodium sulfate
  4. distillationthe solvents were distilled under reduced pressure
  5. customa rotary evaporator
  6. distillationThe residue was subjected to fractional vacuum distillation

出典と根拠

ORDレコード
ord-a464820381884a79b207662cc2d7ea62
出典データセット
uspto-grants-2007_04
特許番号
US07208145B2

反応ノート

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