Potassium bis(trimethylsilyl)amide → HCID 68541212, compound

HRID 1992958Notes

Reaction equation

HRID 1992958 reaction equation
[C:1]([C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[C:19](=[O:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1(C)C=CC=CC=1>[CH3:18][O:17][C:15]1[CH:16]=[C:11]2[C:12](=[CH:13][CH:14]=1)[C:19]([OH:27])=[C:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:1]2

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 68534724HCID 68534724, compound

Product 1

HCID 68541212HCID 68541212, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1-[2-(1-decyn-1-yl)-4-(methyloxy)phenyl]-2-phenylethanone (192) (0.80 g, 2.21 mmol) in toluene was treated with a KHMDS solution in toluene to give 0.60 g (75%) of the title compound (193) as a light brown oil. 1H NMR (400 MHz, CDCl3): δ 0.85 (t, J=7.1 Hz, 3H), 1.10-1.30 (m, 10H), 1.35-1.50 (m, 2H), 2.46 (t, J=7.3 Hz, 2H), 3.93 (s, 3H), 5.16 (s, 1H), 7.06-7.10 (m, 2H), 7.22 (s, 1H), 7.32-7.37 (m, 2H), 7.42-7.48 (m, 1H), 7.50-7.56 (m, 2H), 8.08 (d, J=9.8 Hz, 1H). LCMS (ESI): m/z 363 (M+H)+, m/z 361 (M−H)−.

Sources & evidence

ORD record
ord-e31456a191624c46be6b9958dfa95481
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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