Ethanol → 4,6-Difluoro-2-methyl-indan-1-ol

HRID 574638Notes

Reaction equation

HRID 574638 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:13])[C:6]2=[O:12].C(O)C>>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:13])[CH:6]2[OH:12]

Participants

3

Reactant 2

HCID 702EthanolHCID 224570084,6-Difluoro-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 797261264,6-Difluoro-2-methyl-indan-1-olYield 50.6%

Procedure

According to Scheme 3, step 2: to a solution 4,6-Difluoro-2-methyl-indan-1-one (7a) (1.27 g, 6.97 mmol) in ethanol (30 ml) NaBH4 (0.26 g, 6.97 mmol) was added in portions at 0° C. and then the mixture was stirred at room temperature for 18 h. After evaporation of solvents in vacuo, water was added to the residue, the solution was extracted 3 times with ethyl acetate, then 2N aqueous HCl was added and the combined organic layers were washed with saturated aq. NaHCO3 and water. After drying over Na2SO4 and filtration, solvents were evaporated in vacuo to give 650 mg 4,6-Difluoro-2-methyl-indan-1-ol (8a) which was used immediately in the next step without purification.

Workup

  1. customAfter evaporation of solvents in vacuo, water
  2. additionwas added to the residue
  3. extractionthe solution was extracted 3 times with ethyl acetate
  4. addition2N aqueous HCl was added
  5. washthe combined organic layers were washed with saturated aq. NaHCO3 and water
  6. dry with materialAfter drying over Na2SO4 and filtration, solvents
  7. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-ae546659432f4eebb517ce5bbfb527d4
Source dataset
uspto-grants-2015_05
Patent number
US09034897B2

Reaction notes

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