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

HRID 567193

Reaction equation

HRID 567193 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]>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

3

Reactant 1

HCID 15434585Methyl (5-fluoro-2-methyl-1H-inden-3-yl)acetate

Product 1

HCID 139332935-fluoro-2-methyl-1H-3-indenyl-(2-hydroxy) ethaneYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-fluoro-2-methyl-3-indenyl-acetate (24 g) in dry THF (300 ml) lithiumaluminum hydride (6.9 g) is added. The mixture is stirred at room temperature for 1.5 hours. Excess LiAlH4 is destroyed with saturated aqueous NaHSO4 solution. The organic phase is concentrated in vacuo, and the crude product is purified via silica gel column chromatography elution with methylene chloride. The residue is recrystallized from hexane to give 5-fluoro-2-methyl-1H-3-indenyl-(2-hydroxy)ethane (yield 63%; m.p. 65°-66.5° C).

Workup

  1. customExcess LiAlH4 is destroyed with saturated aqueous NaHSO4 solution
  2. concentrationThe organic phase is concentrated in vacuo
  3. customthe crude product is purified via silica gel column chromatography elution with methylene chloride
  4. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-c2aafcaed40e4648985425e439e6c712
Source dataset
uspto-grants-2001_01
Patent number
US06177471B1

Linked notes

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