Tetrabutylammonium Fluoride → HCID 17981372, compound

HRID 495221Notes

Reaction equation

HRID 495221 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([CH:21]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]#[C:31][Si](C)(C)C)=[CH:26][CH:25]=1)[CH3:20]>O1CCCC1>[CH2:19]([CH:21]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:22][O:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]#[CH:31])=[CH:28][CH:29]=1)[CH3:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 17981367HCID 17981367, compound

Product 1

HCID 17981372HCID 17981372, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 13.2 mL, 13.2 mmol) was added to a stirred solution of [4-(2-ethylhexyloxy)phenylethynyl]trimethylsilane (3) (2.59 g, 13.2 mmol) in tetrahydrofuran (70 mL) and the solution stirred under nitrogen at room temperature for 100 min. The solvent was removed and the residue passed through a plug of silica with dichloromethane—light petroleum (1:9) as eluent to give 1-(2-ethylhexyloxy)-4-ethynylbenzene (4) (1.96 g, 99%) as a pale yellow-brown oil. (Found: C, 83.4, H, 9.85, C19H30OSi requires C, 83.4; H, 9.6%); νmax(film)/cm−1 3294 and 3317 (C≡C—H) and 2107 (C≡C); δH(400 MHz, CDCl3) 0.94 (6 H, m, CH3), 1.28-1.57 (8 H, m, CHCH2CH2CH2CH3 and CHCH2CH3), 1.74 (1H, m, OCH2CH), 3.01 (1 H, s, CCH), 3.85 (2 H, d, J 5, OCH2CH), and 6.85 and 7.43 (4 H, AA′BB′, phenyl H); δc(100.6 MHz, CDCl3) 11.1, 14.1, 23.0, 23.8, 29.0, 30.4, 39.3, 70.5, 75.6, 83.8, 113.7, 114.4, 133.5, 159.8.

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-0657d034a48743599efaf5814653968e
Source dataset
uspto-grants-2009_05
Patent number
US07537842B2

Reaction notes

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