5-Fluoro-1-indanone → 5-Fluoro-2,3-dihydro-1H-inden-1-ol

HRID 2089466Notes

Reaction equation

HRID 2089466 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 1365375-Fluoro-1-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 230828905-Fluoro-2,3-dihydro-1H-inden-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-fluoroindanone (CAS#700-84-5, 0.942 g, 6.274 mmol) in methanol (15 mL) at 0° C. is added sodium borohydride (0.356 g, 9.411 mmol) in one portion. The cooling bath is removed and after 2 hours, the mixture is poured into water (100 mL) and the volatile organics are removed in vacuo. Extraction with dichloromethane, drying over magnesium sulfate, filtering through a cotton plug and concentration affords 5-fluoro-indan-1-ol, which is used in the next step without further purification.

Workup

  1. customThe cooling bath is removed and after 2 hours
  2. additionthe mixture is poured into water (100 mL)
  3. customthe volatile organics are removed in vacuo
  4. extractionExtraction with dichloromethane
  5. dry with materialdrying over magnesium sulfate
  6. filtrationfiltering through a cotton plug and concentration

Sources & evidence

ORD record
ord-df36559a14e84ed39e2af6706c18d772
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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