Tetrahydrofuran → HCID 12079588, compound

HRID 1176167Notes

Reaction equation

HRID 1176167 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:25]=[CH:24][C:10]([N:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:9][CH:8]=1)(C)C.C([O-])([O-])=O.[K+].[K+].C1COCC1>CO>[C:6]([C:7]1[CH:25]=[CH:24][C:10]([N:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:9][CH:8]=1)#[CH:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 12079586HCID 12079586, compound

Product 1

HCID 12079588HCID 12079588, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-[(Trimethylsilyl)ethynyl]-N,N-dihexylaniline (1.206 g, 3.37×10−3 mol), K2CO3 (0.558 g, 4.04×10−3 mol), THF (20 ml) and MeOH (20 ml) were added to a 100-ml round-bottom flask. The reaction mixture was stirred at room temperature for 4.5 h under Ar. After the solvent was evaporated, the residue was chromatographed on silica gel with 4:1 hexane:CHCl3 as the eluent. Yield=0.858 g (89% based on 1.206 g of 4-[(trimethylsilyl)ethynyl]-N,N-dihexylaniline). 1H NMR (250 MHz, CDCl3): δ 7.32 (d, 2H, J=8.9 Hz, Ph), 6.52 (d, 2H, J=8.9 Hz, Ph), 3.25 (t, 4H, J=7.7 Hz, —NCH2—), 2.96 (s, 1H, ethynyl-H), 1.46-1.64 (m, 4H, —NCH2CH2—), 1.20-1.42 (m, 12H, —CH2—), 0.90 (t, 6H, J=6.6 Hz, —CH3). CI MS m/z: 286.253 ((M+H)+) (calcd 286.253).

Workup

  1. customAfter the solvent was evaporated
  2. customthe residue was chromatographed on silica gel with 4:1 hexane

Sources & evidence

ORD record
ord-8a3651b633084d56822c261990d87807
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

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