Di-i-propylphosphine → HCID 178460670, compound

HRID 1072269Notes

Reaction equation

HRID 1072269 reaction equation
O[CH2:2][C-:3]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4]1.[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15].[CH:16]([PH:19][CH:20]([CH3:22])[CH3:21])([CH3:18])[CH3:17]>C(O)(=O)C>[CH:16]([P:19]([CH2:2][C-:3]1[CH:7]=[CH:6][C:5]([CH2:8][P:19]([CH:14]([CH3:13])[CH3:10])[CH:16]([CH3:18])[CH3:17])=[CH:4]1)[CH:20]([CH3:22])[CH3:21])([CH3:18])[CH3:17].[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Fe+2:15]

Participants

4

Reactant 2

HCID 536496Di-i-propylphosphineHCID 1296777371,3-Bis-(hydroxymethyl)ferrocene

Product 1

HCID 178460670HCID 178460670, compoundYield 175.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

2.46 g (10 mmol) of 1,3-bis(hydroxymethyl)ferrocene and 4.72 g (40 mmol) of diisopropylphosphine were added to 40 ml of acetic acid. The resulting mixture was heated at 80° C. for 3.5 hours and extracted with benzene after cooling. The organic phase was then washed with water and then dried over Na2SO4. After evaporation an orange residue was chromatographed on an alumina column. Elution with an ether-light petroleum mixture yielded 3.92 g (88%) of the product. Selected NMR data (CDCl3, 22° C.) 1H: δ0.92 (m, 24H, CH3), 1.63 (m, 4H, CH(CH3)2), 2.49 (bs, 4H, CH2P), 3.92 (s, 5H, C5H5), 3.95 (bs, 2H, 4.5-H), 4.06 (bs, 1H, 2-H). 31P NMR (CDCl3, 22° C.): δ 10.97(s, 2P).

Workup

  1. extractionextracted with benzene
  2. temperatureafter cooling
  3. washThe organic phase was then washed with water
  4. dry with materialdried over Na2SO4
  5. customAfter evaporation an orange residue
  6. customwas chromatographed on an alumina column
  7. washElution with an ether-light petroleum mixture

Sources & evidence

ORD record
ord-96bf738a4d2c4a24a3ffaab036618fc6
Source dataset
uspto-grants-2005_06
Patent number
US06909009B2

Reaction notes

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