Ethyl 2-(2-methyl-1,3-dioxolan-2-yl)butanoate → 2-(2-Methyl-[1,3]dioxolan-2-yl)-butan-1-ol

HRID 1024346

반응식

HRID 1024346 반응식
C([O:3][C:4](=O)[CH:5]([C:8]1([CH3:13])[O:12][CH2:11][CH2:10][O:9]1)[CH2:6][CH3:7])C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:13][C:8]1([CH:5]([CH2:6][CH3:7])[CH2:4][OH:3])[O:9][CH2:10][CH2:11][O:12]1

참가 물질

4

반응물 2

HCID 12948748Ethyl 2-(2-methyl-1,3-dioxolan-2-yl)butanoateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 597350812-(2-Methyl-[1,3]dioxolan-2-yl)-butan-1-ol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

2-(2-Methyl-[1,3]dioxolan-2-yl)-butyric acid ethyl ester (85.5 g) was taken up in dry Et2O (50 mL). This mixture was added dropwise to a suspension of LiAlH4 (16.1 g) in dry Et2O (200 mL), cooled in an ice bath. The mixture was refluxed for 4 h., cooled in an ice bath, and quenched by adding H2O (16.1 mL), 2M aqueous NaOH (32.2 mL) and again H2O (16.1 mL). The suspension was filtered, the filter cake was washed with Et2O, and the combined filtrates were evaporated to dryness. The residue (49 g) was purified by vacuum distillation (112-125° C., 15 mbar), yielding 43.5 g of a clear, colorless liquid. 1H NMR (400 MHz, CDCl3) δ 0.98 (t, J=7.5 Hz, 3H), 1.10-1.24 (m, 1H), 1.31 (s, 3H), 1.50-1.75 (m, 2H), 3.12, (br s, 1H), 3.59-3.76 (m, 2H), 3.94-4.02 (m, 4H).

후처리

  1. temperaturecooled in an ice bath
  2. temperatureThe mixture was refluxed for 4 h.
  3. temperaturecooled in an ice bath
  4. customquenched
  5. additionby adding H2O (16.1 mL), 2M aqueous NaOH (32.2 mL) and again H2O (16.1 mL)
  6. filtrationThe suspension was filtered
  7. washthe filter cake was washed with Et2O
  8. customthe combined filtrates were evaporated to dryness
  9. distillationThe residue (49 g) was purified by vacuum distillation (112-125° C., 15 mbar)
  10. customyielding 43.5 g of a clear, colorless liquid

출처 및 근거

ORD 기록
ord-fd14060e71f543e0af53248d9aaabbb7
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722887B2

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