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

HRID 1992897Notes

Reaction equation

HRID 1992897 reaction equation
[C:1]([C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[C:16](=[O:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1(C)C=CC=CC=1>[CH3:15][O:14][C:12]1[CH:13]=[C:8]2[C:9](=[CH:10][CH:11]=1)[C:16]([OH:24])=[C:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:1]2

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 68539382HCID 68539382, compound

Product 1

HCID 685347346-(Methyloxy)-3-pentyl-2-phenyl-1-naphthalenolYield 74%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1-[2-(1-heptyn-1-yl)-4-(methyloxy)phenyl]-2-phenylethanone (112) (0.57 g, 1.78 mmol) in toluene was treated with a KHMDS solution in toluene to give 0.42 g (74%) of compound 113 as a light brown viscous oil. 1H NMR (400 MHz, CDCl3): δ 0.78 (t, J=6.9 Hz, 3H), 1.10-1.25 (m, 4H), 1.35-1.50 (m, 2H), 2.47 (t, J=7.9 Hz, 2H), 3.93 (s, 3H), 5.16 (s, 1H), 7.06-7.12 (m, 2H), 7.23 (s, 1H), 7.32-7.38 (m, 2H), 7.43-7.49 (m, 1H), 7.50-7.56 (m, 2H), 8.08 (d, J=10.0 Hz, 1H). LCMS (ESI): m/z 321 (M+H)+, m/z 319 (M−H)−.

Sources & evidence

ORD record
ord-eda3780388f54a6e9b6b68046fe7a8e2
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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