Chloride → 2-tert-Butyl-2,3-dihydro-1H-inden-1-one

HRID 1937031Notes

Reaction equation

HRID 1937031 reaction equation
[Cl-].[CH3:2][Mg]I.[C:5](=[C:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:17])([CH3:7])[CH3:6].[Cl-].[NH4+]>O1CCCC1>[C:5]([CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:17])([CH3:2])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 312ChlorideHCID 25517Ammonium ChlorideHCID 15133342-isopropylidene-1-indanoneHCID 178418373HCID 178418373, compound

Product 1

HCID 129273752-tert-Butyl-2,3-dihydro-1H-inden-1-oneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the cupurous chloride (0.258 g, 2.61 mmol) inside 250 mL round bottom flask was added 22 mL of methylmagnesium iodide (3.0 M solution in diethyl ether, 66 mmol) at 0° C. under nitrogen. Diethyl ether was removed in vacuo. Tetrahydrofuran (65 mL) was then introduced. To this resulting suspension was added a solution of 2-isopropylidene-1-indanone (5.00 g, 29 mmol) in Tetrahydrofuran (25 mL) through a dropping funnel dropwise at 0° C. The mixture was stirred at the same temperature for another 1 h and then at ambient temperature overnight (16 h). The slurry was poured into ice (32 g) containing ammonium chloride (6.44 g). The solution was extracted with diethyl ether (5*80 mL). All ethereal layers were combined, washed with water (20 mL), dried over anhydrous magnesium sulfate and concentrated to yield 5.29 g (97%) of 2-t-butyl-1-indanone. H-NMR (CDCL3) δ 0.95 (s, 9H), 2.38 (dd, J=4.3, 8.0 Hz, 1 H), 2.90 (dd, J=4.3, 17.4 Hz, 1H), 3.08 (dd, J=8.0, 17.4 Hz, 1H) 7.23 (br t, J=7.4 Hz, 1H), 7.35 (br d, J=7.6 Hz, 1H), 7.46 (br t, J=7.6 Hz, 1H), 7.61 (br d, J=7.4 Hz, 1H):

Workup

  1. customDiethyl ether was removed in vacuo
  2. additionTetrahydrofuran (65 mL) was then introduced
  3. customat ambient temperature
  4. customovernight (16 h)
  5. extractionThe solution was extracted with diethyl ether (5*80 mL)
  6. washwashed with water (20 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fee512d3658149189593c90dcc71fcd6
Source dataset
uspto-grants-2002_05
Patent number
US06391991B1

Reaction notes

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