Chlorotrimethylsilane → HCID 21469535, compound

HRID 1938726Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][Si:14](Cl)([CH3:16])[CH3:15].[CH3:18][C:19](=[O:32])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:13][Si:14]([CH3:16])([CH3:15])[O:32][C:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH2:18]

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred, room temperature solution of diisopropylamine (49 mL, 0.35 mol) in dry THF (500 mL) was added a 2.06M solution (170 mL, 0.35 mol) of n-butyl lithium in hexanes in one portion. The solution was cooled to -78° C. To the stirred solution was added neat trimethylsilylchloride (213 mL, 1.68 mol) over 6 minutes. Stirred for 6 minutes. To this solution was added a solution of 2-tetradecanone (71.40 g, 0.3362 mol) in dry THF (710 mL) over 33 minutes. Stirred 5 minutes. To the mixture was added triethylamine (375 mL, 2.7 mol) over 6 minutes followed by a saturated sodium bicarbonate solution (780 mL). The mixture was allowed to warm. When the temperature reached 0° C., petroleum ether (1.7 L) was added, and the organic layer was washed with chilled H2O (2×1.4 L), chilled 0.1M citric acid (3×2 L) and saturated NaCl. The organic layer was dried (Na2SO4) and rotoevaporated and dried in vacuo to give a yellow oil; yield 97.6 g (102%).

Workup

stirringStirred 5 minutes
temperatureto warm
customreached 0° C.
washthe organic layer was washed with chilled H2O (2×1.4 L)
temperaturechilled 0.1M citric acid (3×2 L) and saturated NaCl
dry with materialThe organic layer was dried (Na2SO4)
customdried in vacuo
customto give a yellow oil

Sources & evidence

ORD record: ord-78dac6cf879747cbb5204bc865de1cc8
Source dataset: uspto-grants-1997_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05693657

Reaction notes

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