Potassium bis(trimethylsilyl)amide → 6-(Methyloxy)-3-(2-methylpropyl)-2-phenyl-1-naphthalenol

HRID 1992890Notes

Reaction equation

HRID 1992890 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:18]#[C:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH:4]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][CH:8]=1)[C:9]([OH:17])=[C:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:19]([CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:18]2

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 685346851-[4-(Methyloxy)-2-(4-methyl-1-pentyn-1-yl)phenyl]-2-phenylethanone

Product 1

HCID 685409276-(Methyloxy)-3-(2-methylpropyl)-2-phenyl-1-naphthalenolYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1-[4-(methyloxy)-2-(4-methyl-1-pentyn-1-yl)phenyl]-2-phenylethanone (104) (0.73 g, 2.39 mmol) in toluene was treated with a KHMDS solution in toluene to give 0.66 g (91%) of the title compound (105) as a light yellow viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.73 (d, J=6.8 Hz, 6H), 1.55-1.70 (m, 1H), 2.38 (d, J=7.1 Hz, 2H), 3.93 (s, 3H), 5.15 (s, 1H), 7.05-7.10 (m, 2H), 7.18 (s, 1H), 7.30-7.36 (m, 2H), 7.42-7.48 (m, 1H), 7.49-7.55 (m, 2H), 8.08 (d, J=8.8 Hz, 1H). LCMS (APCI): m/z 307 (M+H)+.

Sources & evidence

ORD record
ord-f44a02a8a3204ebf8ad8f9c8f8ca3d1d
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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