Sodium borohydride → 3,3-Difluoro-2,2-dimethylindan-1-ol

HRID 2089502Notes

Reaction equation

HRID 2089502 reaction equation
[F:1][C:2]1([F:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[C:3]1([CH3:13])[CH3:12].[BH4-].[Na+]>C(O)C>[F:1][C:2]1([F:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([OH:11])[C:3]1([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 591993933,3-Difluoro-2,2-dimethyl-1-indanone

Product 1

HCID 591993313,3-Difluoro-2,2-dimethylindan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3,3-difluoro-2,2-dimethyl-indan-1-one (520 mg, 2.65 mmol) in ethanol (15 mL) is added NaBH4 (100 mg, 2.65 mmol). After 15 minutes the reaction is quenched with saturated aqueous NH4Cl and concentrated to near dryness. The resulting residue is diluted with ethyl acetate and washed with brine, dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:6) to provide 3,3-difluoro-2,2-dimethyl-indan-1-ol; 1H NMR (400 MHz, CDCl3) δ ppm 1.07 (d, J=2.3 Hz, 2 H), 1.27 (d, J=2.3 Hz, 2 H), 4.79-4.83 (m, 1 H), 7.41-7.46 (m, 1 H), 7.48-7.60 (m, 3 H).

Workup

  1. customAfter 15 minutes the reaction is quenched with saturated aqueous NH4Cl
  2. concentrationconcentrated
  3. additionThe resulting residue is diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:6)

Sources & evidence

ORD record
ord-5ff8ed3b7c3446c6af5c099e9d41b2bf
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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