Water → 6-Isobutoxyindan-1-one

HRID 1965069Notes

Reaction equation

HRID 1965069 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:19][CH:20]([CH3:22])[CH3:21].O>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1)[CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 70206596-Hydroxy-1-indanone

Product 1

HCID 440728476-Isobutoxyindan-1-oneYield 72.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6-hydroxy-2,3-dihydro-1H-inden-1-one (5.0 g, 33.8 mmol) in DMF (170 mL) was added K2CO3 (9.33 g, 67.5 mmol) and 1-bromo-2-methylpropane (5.50 mL, 50.6 mmol). The resulting orange mixture was stirred at r.t. overnight and was then heated to 60° C. for 2 days. The mixture was cooled to r.t., water was added and the mixture was extracted with EtOAc (×4). The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography using 0-20% EtOAc in heptane as eluent afforded 4.98 g (72% yield) of the title compound: 1H NMR (500 MHz, CDCl3) δ ppm 1.03 (d, 6 H), 2.10 (dt, 1 H), 2.69-2.75 (m, 2 H), 3.04-3.11 (m, 2 H), 3.75 (d, 2 H), 7.17-7.22 (m, 2 H), 7.37 (d, 1 H); MS (ES+) m/z 205 [M+H]+.

Workup

  1. temperaturewas then heated to 60° C. for 2 days
  2. temperatureThe mixture was cooled to r.t.
  3. extractionthe mixture was extracted with EtOAc (×4)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography

Sources & evidence

ORD record
ord-80c6567a5c9b4faeaea5015ddca20ee5
Source dataset
uspto-grants-2013_04
Patent number
US08415483B2

Reaction notes

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