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

HRID 1690770Notes

Reaction equation

HRID 1690770 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), in ethanol (80 mL) at −30° C. is added a solution of NaBH4 (29 mg, 0.74 mmol) in ethanol (3 mL). After one h 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 twice 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 h 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 twice 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-6ac45984c92841d9be45888f6d202f24
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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