2,2-dimethyl-2,3-dihydro-1H-inden-1-one → 2,3-Dihydro-2,2-dimethyl-1H-inden-1-ol

HRID 2089484Notes

Reaction equation

HRID 2089484 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:11].[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH3:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[OH:11]

Participants

4

Reactant 2

HCID 3012022,2-dimethyl-2,3-dihydro-1H-inden-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 109427712,3-Dihydro-2,2-dimethyl-1H-inden-1-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,2-dimethyl-indan-1-one, which can be prepared as described in Ranu, B. C.; Jana, U. Journal of Organic Chemistry, 1999, 64, 6380-6386, (13.0 g, 81.3 mmol) in methanol (200 mL) at −20° C. is added NaBH4 (3.07 g, 81.3 mmol). Upon complete consumption of the starting ketone, as determined by TLC analysis, the reaction is quenched with saturated aqueous NH4Cl. The reaction mixture is then concentrated to near dryness, diluted with ethyl acetate and washed with water. The organic layer is then dried with Na2SO4, filtered, and concentrated. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:8) to provide 2,2-dimethyl-indan-1-ol. 1H NMR (400 MHz, CDCl3) δ ppm 1δ ppm 1.05 (s, 3 H), 1.20 (s, 3 H), 2.56-2.89 (m, 2 H), 4.70 (s, 1 H), 7.16-7.26 (m, 3 H), 7.35-7.42 (m, 1 H).

Workup

  1. customUpon complete consumption of the starting ketone
  2. customthe reaction is quenched with saturated aqueous NH4Cl
  3. concentrationThe reaction mixture is then concentrated
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer is then dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:8)

Sources & evidence

ORD record
ord-43cdb17aa4ae4eb099ebf12d79faed40
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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