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

HRID 1706157Notes

Reaction equation

HRID 1706157 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 mol) of acetylferrocene in 200 ml of ethanol was added dropwise, at room temperature, to a solution of 30.4 g (0.8 mol) of sodium borohydride in 200 ml of water. The reaction mixture was stirred overnight at room temperature poured into water and the solid material which was obtained was filtered off. The product was washed and dried. 40 g of 1-hydroxyethylferrocene of melting point 69° C. were obtained in this manner.

Workup

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

Sources & evidence

ORD record
ord-19bc665c72fd4381ab5063071c05ef45
Source dataset
uspto-grants-1980_06
Patent number
US04206227

Reaction notes

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