Aluminium lithium hydride → 1,3-Bis-(hydroxymethyl)ferrocene

HRID 1072268Notes

Reaction equation

HRID 1072268 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C-:12]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13]1)=O)C.[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24]>CCOCC>[OH:9][CH2:10][C-:12]1[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13]1.[CH-:19]1[CH:23]=[CH:22][CH:21]=[CH:20]1.[Fe+2:24]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178468928HCID 178468928, compound

Product 1

HCID 1296777371,3-Bis-(hydroxymethyl)ferroceneYield 77.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirring suspension of 60 mg (15.7 mmol) of lithium aluminum hydride in 30 ml of ether was added dropwise to a solution of 150 mg (0.56 mmol) of 1-ethoxycarbonyl-3-formylferrocene in ether (30 ml). Stirring was continued for 4.5 hours at room temperature. The mixture was then quenched with saturated aqueous solution of NH4Cl, and 30 ml of ether was added to the resulting solution. After separation of the organic and aqueous layers, the latter was extracted twice with ether and the combined organic solutions were then washed with water and dried over Na2SO4. Evaporation of the solvent yielded 100 mg (77.5%) of yellow crystals. Selected NMR data 1H (acetone-d6, 22° C.): δ4.11 (s, 5H,C5H5), 4.13 (d, 2H, 4.5-H), 4.25 (t,1H, 2-H), 429 (s, 4H, CH2)

Workup

  1. customThe mixture was then quenched with saturated aqueous solution of NH4Cl, and 30 ml of ether
  2. additionwas added to the resulting solution
  3. customAfter separation of the organic and aqueous layers
  4. extractionthe latter was extracted twice with ether
  5. washthe combined organic solutions were then washed with water
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-502c1747108e4e97b0c311681aa5d85d
Source dataset
uspto-grants-2005_06
Patent number
US06909009B2

Reaction notes

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