1-(2,3-Dihydro-1H-inden-4-yl)ethan-1-one → HCID 21908341, compound

HRID 1374624Notes

Reaction equation

HRID 1374624 reaction equation
[CH3:1][Mg]Br.[C:4]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][CH2:11]2)(=[O:6])[CH3:5]>C1(C)C=CC=CC=1.C1COCC1.C1COCC1.C(OCC)(=O)C>[OH:6][C:4]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH2:10][CH2:11]2)([CH3:1])[CH3:5]

Participants

6

Reactant 2

HCID 136579611-(2,3-Dihydro-1H-inden-4-yl)ethan-1-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 21908341HCID 21908341, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

10 ml (14 mmol) of a 1.4 M methylmagnesium bromide solution in toluene-THF (3:1) is added in drops at 0° C. to a solution of 1.6 g (10 mmol) of 4-acetylindan (F. Dallacker, J. Van Wersch, Chem. Ber. 1972, 105, 2565) in 40 ml of THF. After 30 minutes at 0° C. and 1.5 hours at room temperature, the batch is diluted with 200 ml of ethyl acetate, washed with 1 M hydrochloric acid and saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography of the residue on silica gel with hexane-ethyl acetate yields 0.64 g of product.

Workup

  1. washwashed with 1 M hydrochloric acid and saturated NaCl
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-e6d8b4c0f6a446299fa072825f27b55d
Source dataset
uspto-grants-2007_01
Patent number
US07166592B2

Reaction notes

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