Sodium borohydride → Cyclopenta-1,3-diene;1-cyclopenta-2,4-dien-1-ylethanol;iron(2+)

HRID 972383Notes

Reaction equation

HRID 972383 reaction equation
[C:1]([C-:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)(=[O:3])[CH3:2].[CH-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.[Fe+2:14].[BH4-].[Na+]>C(O)C.O>[OH:3][CH:1]([C-:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)[CH3:2].[CH-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.[Fe+2:14]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178466060HCID 178466060, compound

Product 1

HCID 15242028Cyclopenta-1,3-diene;1-cyclopenta-2,4-dien-1-ylethanol;iron(2+)Yield 86.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 46.2 g (0.2 mole) of acetylferrocene in 200 ml of ethanol was added dropwise, at room temperature, to a solution of 30.4 g (0.8 mole) of sodium borohydride in 200 ml of water. The reaction mixture was stirred overnight at room temperature and poured into water and the solid obtained was filtered off. The product was washed and dried. In this way, 40 g of 1-hydroxyethylferrocene with a melting point of 69° C were obtained.

Workup

  1. customthe solid obtained
  2. filtrationwas filtered off
  3. washThe product was washed
  4. customdried

Sources & evidence

ORD record
ord-d36ccd1f6f174ff1a9d2ba48c0b43628
Source dataset
uspto-grants-1977_10
Patent number
US04053296

Reaction notes

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