Water → HCID 23538038, compound

HRID 1792382Notes

Reaction equation

HRID 1792382 reaction equation
[CH2:1]([OH:6])[CH2:2][CH2:3][C:4]#[CH:5].[H-].[Na+].Br[CH2:10][CH2:11][CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].O>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[Si:14]([O:13][CH2:12][CH2:11][CH2:10][O:6][CH2:1][CH2:2][CH2:3][C:4]#[CH:5])([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:16])[CH3:15]

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 793464-Pentyn-1-olHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilane

Product 1

HCID 23538038HCID 23538038, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-pentyn-1-ol (2.1 g, 26.1 mmol) in dry N,N-dimetylformamide (100 ml) was added sodium hydride (1.04 g, 60% in oil, 26.1 mmol) at room temperature. The mixture was stirred for 40 minutes, and 1-bromo-3-(t-butyldimethylsilyloxy) propane (4.4 g, 17.4 mmol) was added thereto. The mixture was stirred at room temperature for 2 hours. After the reaction was completed, water was added thereto. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and filtered. The organic solvent was removed under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=20:1) to give the title compound (920 mg, yield: 21%).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 hours
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe organic solvent was removed under reduced pressure
  7. customto give a crude product
  8. customThis crude product thus obtained

Sources & evidence

ORD record
ord-d4473e85e2974a549bde94f5d4c89367
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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