Reaction equation
[CH:1](NC(C)C)(C)C.[CH2:8]([Li])CCC.[Li+].CC([N-]C(C)C)C.[C:21]1(=[O:30])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22]1.[C:31]([C:33]([O:35][CH3:36])=[O:34])#N>C1COCC1>[CH3:1][CH:22]1[CH2:23][C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]1=[O:30].[CH3:8][C:31]1([C:33]([O:35][CH3:36])=[O:34])[CH2:23][C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:21]1=[O:30]Participants
Reactant 5
Product 2
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of diisopropylamine (2.06 mL, 14.6 mmol) in THF (14 mL) at 0° C. was a solution of n-butyl lithium (5.55 mL of a 2.5 M in solution in hexanes; 14.6 mmol), dropwise over 15 min. Meanwhile, a solution of 2-methyl-1-indanone (2.03 g, 13.9 mmol) in THF (10 mL) was prepared and cooled to −78° C. under N2. After 30 minutes the above solution of LDA was cooled to −78° C. and added to the above solution of indanone, dropwise over 15 min via double-ended needle. The mixture was stirred 30 min and methyl cyanoformate (1.32 mL, 16.7 mmol) was added. The mixture was stirred 40 minutes, gradually warming ca. to −20° C., quenched with satd NH4Cl and extracted with Et2O (2×25 mL). Combined organics were washed (brine), dried over Na2SO4 and concentrated in vacuo, affording the title compound which was used without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 1.52 (s, 3H), 3.00 (d, J=17.3 Hz, 1 H), 3.67-3.73 (m, 4H), 7.41 (t, J=7.57 Hz, 1H), 7.47 (m, 1H), 7.63 (m, 1 H), 7.79 (d, J=7.57 Hz, 1 H).
Workup
- customat 0° C.
- stirringThe mixture was stirred 40 minutes
- temperaturegradually warming ca. to −20° C.
- customquenched with satd NH4Cl
- extractionextracted with Et2O (2×25 mL)
- washCombined organics were washed (brine)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-a78e7e593c0f430a81e9fb40ea85cb19
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822518B2
Linked notes
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