Potassium bis(trimethylsilyl)amide → 3-Butyl-2-(4-fluorophenyl)-1-naphthalenol

HRID 1992936Notes

Reaction equation

HRID 1992936 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]#[C:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:10])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1(C)C=CC=CC=1>[CH2:19]([C:18]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[C:9]([OH:10])[C:11]2[C:12]([CH:17]=1)=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 685385242-(4-Fluorophenyl)-1-[2-(1-hexyn-1-yl)phenyl]ethanone

Product 1

HCID 685361133-Butyl-2-(4-fluorophenyl)-1-naphthalenolYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 2-(4-fluorophenyl)-1-[2-(1-hexyn-1-yl)phenyl]ethanone (165) (0.37 g, 1.24 mmol) in toluene was treated with a KHMDS solution in toluene to give 0.25 g (69%) of the title compound (166) as a yellow solid upon standing. 1H NMR (400 MHz, CDCl3): δ 0.77 (t, J=7.3 Hz, 3H), 1.15-1.30 (m, 2H), 1.35-1.50 (m, 2H), 2.47 (t, J=7.9 Hz, 2H), 5.10 (s, 1H), 7.20-7.28 (m, 2H), 7.30-7.37 (m, 3H), 7.40-7.50 (m, 2H), 7.75 (d, J=8.0 Hz, 1H), 8.17 (d, J=8.4 Hz, 1H). LCMS (APCI): m/z 295 (M+H) t.

Sources & evidence

ORD record
ord-3d3248c58a0e40a1b95d8cb62a62df6c
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

Loading…