5-Fluoro-1-indanone → 5-Fluoro-2,3-dihydro-1H-inden-1-ol
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]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customThe cooling bath is removed and after 2 hours
- additionthe mixture is poured into water (100 mL)
- customthe volatile organics are removed in vacuo
- extractionExtraction with dichloromethane
- dry with materialdrying over magnesium sulfate
- 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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