Aluminium lithium hydride → 2-(2,2-difluoropropylamino)ethanol

HRID 859188Notes

Reaction equation

HRID 859188 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:16])([CH3:15])[C:9]([NH:11][CH2:12][CH2:13][OH:14])=O>C(OCC)C>[F:7][C:8]([F:16])([CH3:15])[CH2:9][NH:11][CH2:12][CH2:13][OH:14]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 26188900HCID 26188900, compound

Product 1

HCID 27583572-(2,2-difluoropropylamino)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of lithium aluminum hydride (5.5 g, 146 mmol) in diethyl ether (85 ml) was added a solution of 2,2-difluoro-N-(2-hydroxy-ethyl)-propionamide (11.2 g, 73 mmol) in diethyl ether (55 ml) dropwise at such a rate to maintain a gentle reflux. After an additional 1.5 hours, the reaction was quenched with sodium sulfate decahydrate, diluted with ethyl acetate and allowed to stir for 18 hours. The mixture was filtered with the aid of diatomaceous earth, washing with ethyl acetate. The filtrate was concentrated in vacuo and fractionally distilled (11 torr, collecting fractions distilling at 75–88° C.) to afford the title compound (I-3c) as a colorless oil, 4.5 g.

Workup

  1. temperatureto maintain a gentle reflux
  2. customthe reaction was quenched with sodium sulfate decahydrate
  3. additiondiluted with ethyl acetate
  4. filtrationThe mixture was filtered with the aid of diatomaceous earth
  5. washwashing with ethyl acetate
  6. concentrationThe filtrate was concentrated in vacuo
  7. distillationfractionally distilled
  8. distillation(11 torr, collecting fractions distilling at 75–88° C.)

Sources & evidence

ORD record
ord-46faf2a20dca41949a90f15cffe2da3c
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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