Methyl (5-fluoro-2-methyl-1H-inden-3-yl)acetate → 5-fluoro-2-methyl-1H-3-indenyl-(2-hydroxy) ethane

HRID 542229

Reaction equation

HRID 542229 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([CH3:11])=[C:5]2[CH2:12][C:13](OC)=[O:14].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([CH3:11])=[C:5]2[CH2:12][CH2:13][OH:14]

Participants

4

Reactant 2

HCID 15434585Methyl (5-fluoro-2-methyl-1H-inden-3-yl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 139332935-fluoro-2-methyl-1H-3-indenyl-(2-hydroxy) ethaneYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 14b (24 g) in dry THF (300 ml), LiAlH4 (6.9 g) was added in portions. The mixture was stirred at room temperature for 1.5 hours. Excess LiAlH4 (LAH) was destroyed with saturated Na2SO4 solution. The organic phase was concentrated in vacuo, and the crude product was purified via silica gel column chromatography eluting with methylene chloride. The product was recrystallized from hexane to give 5-fluoro-2-methyl-1H-3-indenyl-(2-hydroxy)ethane (15b) (14.9 g, 63% yield): m.p. 65°-66.5° C.

Workup

  1. customExcess LiAlH4 (LAH) was destroyed with saturated Na2SO4 solution
  2. concentrationThe organic phase was concentrated in vacuo
  3. customthe crude product was purified via silica gel column chromatography
  4. washeluting with methylene chloride
  5. customThe product was recrystallized from hexane

Sources & evidence

ORD record
ord-caf1133566164e30834c0c7c92913eaf
Source dataset
uspto-grants-1987_04
Patent number
US04656190

Linked notes

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