Aluminium lithium hydride → HCID 66747306, compound

HRID 331698Notes

Reaction equation

HRID 331698 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:14]1([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[CH2:17][NH:16][C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH2:7]([C:14]1([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[CH:20]=2)[CH2:15][NH:16][CH2:17]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66747540HCID 66747540, compound

Product 1

HCID 66747306HCID 66747306, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M lithium aluminium hydride solution in tetrahydrofuran (14 ml, 14 mmol) was added to a stirred solution of 3-benzyl-3-(3-methoxyphenyl)azetidin-2-one (1.7 g, 6.36 mmol) in tetrahydrofuran and heated to reflux for 4 h. The solution was cooled and quenched by careful addition of a 2M sodium hydroxide solution and then extracted with ether. The organic phase was dried over sodium bicarbonate and purified on 12 g SiO2 using 20% methanol in dichloromethane (clear colourless oil). m=520 mg (32%)

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. temperatureThe solution was cooled
  4. customquenched by careful addition of a 2M sodium hydroxide solution
  5. extractionextracted with ether
  6. dry with materialThe organic phase was dried over sodium bicarbonate
  7. custompurified on 12 g SiO2 using 20% methanol in dichloromethane (clear colourless oil)

Sources & evidence

ORD record
ord-d05ef9b01f1d46ad9866b9d3f7732a08
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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