Sodium ethoxide → 6,10,14-Trimethyl-pentadeca-5,9,13-trien-1-yne

HRID 63808Notes

Reaction equation

C[Si](C)(C)[C:3]#[C:4][CH2:5][CH2:6][CH:7]=[C:8]([CH3:20])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17].CC[O-].[Na+]>CC(OC)(C)C.O>[CH3:20][C:8]([CH2:9][CH2:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:7][CH2:6][CH2:5][C:4]#[CH:3]

Participants

Conditions

Temperature: 60 °C

Procedure

A 3-N 250 mL flask was charged with trimethyl-(6,10,14-trimethyl-pentadeca-5,9,13-trien-1-ynyl)-silane (Ex-1B-7) (19.38 g, 64.1 mmol) and NaOEt (42 mL of a 21% w/w solution, 112 mmol). The reaction mixture was stirred at 60° C. for 4 h. After cooling to RT, the reaction mixture was diluted with MTBE (100 mL) and water (100 mL) and then filtered to remove solid present at the phase interface. The aqueous layer was extracted with MTBE (3×100 mL). The combined MTBE layers were washed with brine (100 mL), dried over MgSO4, filtered, and concentrated by rotary evaporation to yield 12.43 g of 6,10,14-trimethyl-pentadeca-5,9,13-trien-1-yne (Ex-1B-8) as a dark orange oil (96%). 1H NMR (400 MHz, CDCl3) δ (ppm): 5.23-5.17 (m, 1H), 5.17-5.07 (m, 2H), 2.29-1.95 (m, 13H), 1.70 (s, 3H), 1.65 (s, 3H), 1.62 (s, 6H).

Workup

temperatureAfter cooling to RT
filtrationfiltered
customto remove solid present at the phase interface
extractionThe aqueous layer was extracted with MTBE (3×100 mL)
washThe combined MTBE layers were washed with brine (100 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record: ord-5d73db12900d4e17adc23f9f8043f057
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447006B2

Reaction notes

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