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Ethanol → 2-Methyltetrahydrofuran

HRID 1183171
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HRID 1183171 반응식
[NH2:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])[CH2:3][C:4]([OH:6])=[O:5].[CH2:14](O)[CH3:15].S(Cl)([Cl:19])=O>CC1CCCO1>[NH2:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])[CH2:3][C:4]([O:6][CH2:14][CH3:15])=[O:5].[ClH:19].[NH2:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])[CH2:3][C:4]([O:6][CH2:14][CH3:15])=[O:5].[CH3:12][CH:7]1[CH2:2][CH2:3][CH2:4][O:5]1
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참가 물질

7

반응물 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 6934180(3S)-3-Amino-3-(2-methylphenyl)propanoic acid

생성물 3

HCID 73012-MethyltetrahydrofuranHCID 7046987HCID 7046987, 화합물HCID 67362509HCID 67362509, 화합물

시약·촉매·용매 1

HCID 7301
2-Methyltetrahydrofuran
용매

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온도
80 °C

실험 절차

(S)-3-Amino-3-(2-methyl-phenyl)propionic acid (10.0 g, 55.8 mmol) was suspended in 2-methyltetrahydrofuran (100 ml) and ethanol (25.7 g, 558 mmol) was added. The mixture was heated to 80° C. and thionyl chloride (6.64 g, 55.8 mmol) was added slowly. After 2 h at 80° C. the solvents were almost completely removed by distillation. After cooling the mixture was stirred at room temperature for 16 h. Then more solvent was removed under reduced pressure to give the title compound in the form of ethyl (S)-3-amino-3-(2-methyl-phenyl)-propionate hydrochloride together with some 2-methyltetrahydrofuran in quantitative yield.

후처리

  1. customAfter 2 h at 80° C. the solvents were almost completely removed by distillation
  2. temperatureAfter cooling the mixture
  3. customThen more solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-acf950f1273d4ad893301f22411be967
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08664257B2

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