2,2-Dimethyl-1H-indene-1,3(2H)-dione → 3-Hydroxy-2,2-dimethyl-1-indanone

HRID 2089507Notes

Reaction equation

HRID 2089507 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:12].[BH4-].[Na+]>C(O)C>[OH:12][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10](=[O:11])[C:2]1([CH3:13])[CH3:1]

Participants

4

Reactant 2

HCID 5999832,2-Dimethyl-1H-indene-1,3(2H)-dioneHCID 4311764Sodium borohydride

Product 1

HCID 130236813-Hydroxy-2,2-dimethyl-1-indanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2,2-dimethyl-indan-1,3-dione (430 mg, 2.47 mmol), which can be prepared as described in Example 18, in ethanol (80 mL) at −30° C. is added a solution of NaBH4 (29 mg, 0.74 mmol) in ethanol (3 mL). After one hour the reaction is quenched with saturated aqueous NH4Cl and the mixture is brought to room temperature. The reaction mixture is concentrated to approximately half of its original volume and then diluted with ethyl acetate and washed with water. The aqueous layer is then back-extracted two times with ethyl acetate. The organic layers are combined, 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 afford 3-hydroxy-2,2-dimethyl-indan-1-one; MS: (ESI) m/z 177.0 (M+H)+.

Workup

  1. customAfter one hour the reaction is quenched with saturated aqueous NH4Cl
  2. customis brought to room temperature
  3. concentrationThe reaction mixture is concentrated to approximately half of its original volume
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. extractionThe aqueous layer is then back-extracted two times with ethyl acetate
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:6)

Sources & evidence

ORD record
ord-9214f877941a49fd8711e44f964e05b5
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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