Potassium Chloride → HCID 23073442, compound

HRID 969589

Reaction equation

HRID 969589 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].[C-]#[C-].[Li+].[CH2:27](N(CC)CCN)[CH3:28].[Li+].[Cl-].[K+]>CS(C)=O>[C:20]([Si:17]([O:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:27]#[CH:28])([CH3:19])[CH3:18])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 4873Potassium ChlorideHCID 1167587414-Bromo-1-(t-butyldimethylsiloxy)tetradecaneHCID 178464060HCID 178464060, compound

Product 1

HCID 23073442HCID 23073442, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

The solution of (14-bromo-tetradecyloxy)-tert-butyl-dimethylsilane (8.9 g, 21.4 mmol, 1 eq) in DMSO (10 mL) was added dropwise to the solution of N,N-diethylethane-1,2-diamine lithium acetylide (3.1 g, 33.2 mmol, 1.5 eq) in DMSO (15 mL) at 0° C. This solution was stirred at room temperature for 6 hours, poured into saturated aqueous solution of potassium chloride (100 mL), and extracted three times with hexane (100 mL). The extract was washed with aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated. The resulting concentrate was subjected to silica gel flush column chromatography (eluate: hexane-CH2Cl2=80-20) to obtain the colorless liquid of the title compound (6.12 g, yield 81%).

Workup

  1. extractionextracted three times with hexane (100 mL)
  2. washThe extract was washed with aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. concentrationThe resulting concentrate
  6. customflush column chromatography (eluate: hexane-CH2Cl2=80-20)

Sources & evidence

ORD record
ord-c9bbc06960394a3cad966d33a13ca9ea
Source dataset
uspto-grants-2007_12
Patent number
US07307098B2

Linked notes

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