Water → 2-Amino-1-(thiophen-3-yl)ethan-1-ol

HRID 1186536Notes

Reaction equation

HRID 1186536 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH:8]([C:11]1[CH:15]=[CH:14][S:13][CH:12]=1)[C:9]#[N:10].O.[OH-].[Na+]>C1COCC1>[NH2:10][CH2:9][CH:8]([C:11]1[CH:15]=[CH:14][S:13][CH:12]=1)[OH:7]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13854064HCID 13854064, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 167680492-Amino-1-(thiophen-3-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a stirred suspension of LAH (8.7 g, 225 mmol) in dry THF (300 mL) was added a solution of hydroxy-thiophen-3-yl-acetonitrile (12.5 mL, 90 mmol) in dry THF (50 mL) dropwise at 0° C. under nitrogen atmosphere. Then the mixture was warmed to 25° C. and stirred overnight. After cooling to 10° C., H2O (8.7 mL) was added to the solution, followed by NaOH solution (8.7 mL, 15%), then H2O (26 mL). The reaction mixture was filtered and the filtrate was concentrated to dryness to afford crude 2-amino-1-thiophen-3-yl-ethanol. (Yield 12.9 g, crude). LC-MS: [M+H]+ 144.

Workup

  1. temperatureAfter cooling to 10° C.
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-3f9758a9328f4cadb1dedab63bca14f5
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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