Ammonium Chloride → HCID 19767477, compound

HRID 1590596Notes

Reaction equation

HRID 1590596 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH:21]1[CH2:24][CH2:23][CH2:22]1)([C:16](OCC)=[O:17])[C:11](OCC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>CCOCC>[CH2:1]([O:8][CH2:9][C:10]([CH:21]1[CH2:24][CH2:23][CH2:22]1)([CH2:11][OH:12])[CH2:16][OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 19767514HCID 19767514, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19767477HCID 19767477, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diethyl 2-benzyloxymethyl-2-cyclobutylmalonate (65 g, 0.19 mol) in dry ether (50 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (11.5 g, 0.3 mol) in dry ether (200 ml) at 0° C. under a nitrogen atmosphere. After the addition, the solution was heated to gentle reflux for 1 hour, allowed to cool and an excess of saturated aqueous ammonium chloride was added. Stirring was continued overnight and the resulting mixture was filtered and the solids washed with ether. The filtrate was extracted with ether, the ether extracts were combined, dried over anhydrous magnesium sulphate and evaporated to leave 2-benzyloxymethyl-2-cyclobutylpropane-1,3-diol (49 g) as an oil.

Workup

  1. additionAfter the addition
  2. temperaturethe solution was heated
  3. temperatureto gentle reflux for 1 hour
  4. temperatureto cool
  5. filtrationthe resulting mixture was filtered
  6. washthe solids washed with ether
  7. extractionThe filtrate was extracted with ether
  8. dry with materialdried over anhydrous magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-6172bdf532a647089c49c05592b0b483
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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