Ethanol → 2-Methyltetrahydrofuran

HRID 1183171Notes

Reaction equation

HRID 1183171 reaction equation
[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

Participants

7

Reactant 3

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

Product 3

HCID 73012-MethyltetrahydrofuranHCID 7046987HCID 7046987, compoundHCID 67362509HCID 67362509, compound

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-acf950f1273d4ad893301f22411be967
Source dataset
uspto-grants-2014_03
Patent number
US08664257B2

Reaction notes

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