Potassium bis(trimethylsilyl)amide → HCID 68539304, compound

HRID 1992924Notes

Reaction equation

HRID 1992924 reaction equation
[CH:1]1([C:4]#[C:5][C:6]2[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=2[C:14](=[O:22])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1(C)C=CC=CC=1>[CH:1]1([C:4]2[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:14]([OH:22])[C:7]3[C:6]([CH:5]=2)=[CH:11][C:10]([O:12][CH3:13])=[CH:9][CH:8]=3)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 68534812HCID 68534812, compound

Product 1

HCID 68539304HCID 68539304, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1-[2-(Cyclopropylethynyl)-4-(methyloxy)phenyl]-2-phenylethanone (151) (0.47 g, 1.62 mmol) in toluene was treated with a KHMDS solution in toluene to give 0.18 g (38%) of the title compound (152) as a light yellow viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.70-0.80 (m, 4H), 1.55-1.65 (m, 1H), 3.91 (s, 3H), 5.22 (s, 1H), 6.92 (s, 1H), 7.00-7.10 (m, 2H), 7.40-7.48 (m, 3H), 7.50-7.57 (m, 2H), 8.07 (d, J=8.9 Hz, 1H). LCMS (APCI): m/z 291 (M+H)+, m/z 289 (M−H)+.

Sources & evidence

ORD record
ord-b6dc38749b4f4834a9fd91f45a1c49a5
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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