Ethyl Lactate → Ethyl 2-benzyloxylactate

HRID 537646노트

반응식

HRID 537646 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 18454908Ethyl 2-benzyloxylactate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6571be00eb5e4cb095785ecde2d44e3d
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865149B2

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