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

HRID 1992940Notes

Reaction equation

HRID 1992940 reaction equation
[C:1]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13](=[O:21])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1(C)C=CC=CC=1>[CH2:3]([C:2]1[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:13]([OH:21])[C:8]2[C:7]([CH:1]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 685346611-[2-(1-Hexyn-1-yl)phenyl]-2-phenylethanone

Product 1

HCID 685362243-Butyl-2-phenyl-1-naphthalenolYield 68.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1-[2-(1-hexyn-1-yl)phenyl]-2-phenylethanone (171) (0.88 g, 3.18 mmol) in toluene was treated with a KHMDS solution in toluene to give 0.60 g (68%) of the title compound (172) as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ 0.76 (t, J=7.3 Hz, 3H), 1.15-1.30 (m, 2H), 1.45-1.55 (m, 2H), 2.49 (t, J=7.8 Hz, 2H), 5.20 (s, 1H), 7.33 (s, 1H), 7.36 (d, J=7.0 Hz, 2H), 7.39-7.50 (m, 3H), 7.50-7.57 (m, 2H), 7.75 (d, J=7.9 Hz, 1H), 8.18 (d, J=8.0 Hz, 1H). LCMS (ESI): m/z 277 (M+H)+, m/z 275 (M−H)−.

Sources & evidence

ORD record
ord-8b4ec10a6443453497f84fd711c21fd2
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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