Potassium bis(trimethylsilyl)amide → HCID 68537345, compound

HRID 1992918Notes

Reaction equation

HRID 1992918 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[O:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1(C)C=CC=CC=1>[CH3:1][O:2][CH2:3][C:4]1[C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:12]([OH:20])[C:7]2[C:6]([CH:5]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 68537290HCID 68537290, compound

Product 1

HCID 68537345HCID 68537345, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1-{2-[3-(methyloxy)-1-propyn-1-yl]phenyl}-2-phenylethanone (144) (0.21 g, 0.79 mmol) in toluene was treated with a KHMDS solution in toluene to give 46 mg (22%) of the title compound (145) as a light brown solid. 1H NMR (400 MHz, CDCl3): δ 3.28 (s, 3H), 4.26 (s, 2H), 5.29 (s, 1H), 7.36-7.42 (m, 2H), 7.44-7.58 (m, 6H), 7.80-7.85 (m, 1H), 8.18-8.24 (m, 1H). LCMS (ESI): m/z 265 (M+H)+, m/z 263 (M−H)−.

Sources & evidence

ORD record
ord-6b8c9f37019a4b9db02d3b2c7fa7452a
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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