Hydrochloric Acid → 1-Undecyn-3-ol, 1-(trimethylsilyl)-

HRID 2081307Notes

Reaction equation

C([Li])CCC.[CH3:6][Si:7]([C:10]#[CH:11])([CH3:9])[CH3:8].[CH:12](=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].Cl>O1CCCC1.C(OCC)C>[CH3:6][Si:7]([CH3:9])([CH3:8])[C:10]#[C:11][CH:12]([OH:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: -70 °C

Procedure

173 mol of n-butyllithium solution (1.6 mol in hexane) is instilled in a solution of 25 g of trimethylsilylacetylene in 500 ml of tetrahydrofuran with stirring and argon atmosphere at -40° C., is stirred for 30 minutes at -40° C., cooled to -70° C. and 48.1 ml of nonanal is instilled at this temperature. After an hour at -70° C., the mixture is allowed to come to -30° C., 300 ml of 2 n hydrochloric acid is added and shaken with diethyl ether. The organic phases are dried (Na2SO4), concentrated by evaporation and the residue is distilled in a bulb tube at 120°-130° C./0.2 mbar. Thus 48.5 of (3RS)-1-(trimethylsilyl)-1-undecin-3-ol is obtained as a colorless oil.

Workup

stirringargon atmosphere at -40° C., is stirred for 30 minutes at -40° C.
waitAfter an hour at -70° C.
customto come to -30° C.
dry with materialThe organic phases are dried (Na2SO4)
concentrationconcentrated by evaporation
distillationthe residue is distilled in a bulb tube at 120°-130° C./0.2 mbar

Sources & evidence

ORD record: ord-7191759d76754a049a8b434818aeedc6
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05183925

Reaction notes

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