Acetic Acid → HCID 86086768, compound

HRID 422490Notes

Reaction equation

HRID 422490 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]#[C:4][CH2:5][CH2:6][CH:7]1[CH2:9][O:8]1.C(O)(=O)C.[Li+].[Br-:17]>C1COCC1>[Br:17][CH2:9][CH:7]([OH:8])[CH2:6][CH2:5][C:4]#[C:3][Si:2]([CH3:11])([CH3:10])[CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 82050Lithium BromideHCID 86086765HCID 86086765, compound

Product 1

HCID 86086768HCID 86086768, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of trimethyl(4-(oxiran-2-yl)but-1-ynyl)silane (4.5 g, 27 mmol) in THF (90 mL) containing acetic acid (4.81 g, 80.21 mmol), was added at 0° C. anhydrous LiBr (3.71 g, 42.78 mmol). The reaction mixture was left stirring overnight at room temperature. The reaction was quenched with saturated NaCl and extracted with Et2O. The organic phase was washed once with a solution of 1M K2CO3 saturated with NaCl, brine, dried over MgSO4, filtered and concentrated. The crude residue was purified over silicagel chromatography (prepacked 70 g silicagel column, from Cyclohexane 100% to DCM 100% as eluent) to afford 2.5 g of 1-bromo-6-(trimethylsilyl)hex-5-yn-2-ol (Yield: 38%) as a yellow oil.

Workup

  1. waitThe reaction mixture was left
  2. customThe reaction was quenched with saturated NaCl
  3. extractionextracted with Et2O
  4. washThe organic phase was washed once with a solution of 1M K2CO3 saturated with NaCl, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified over silicagel chromatography (prepacked 70 g silicagel column, from Cyclohexane 100% to DCM 100% as eluent)

Sources & evidence

ORD record
ord-251a2494a81748268f50f88b0ca5558e
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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