Propargyl bromide → HCID 90010346, compound

HRID 1503473Notes

Reaction equation

HRID 1503473 reaction equation
[H-].[Na+].[CH2:3]([O:10][CH2:11][C:12]([CH3:15])([OH:14])[CH3:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:17][C:18]#[CH:19]>C1COCC1>[CH3:13][C:12]([O:14][CH2:19][C:18]#[CH:17])([CH3:15])[CH2:11][O:10][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 135601221-(Benzyloxy)-2-methylpropan-2-ol

Product 1

HCID 90010346HCID 90010346, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of NaH (5.0 g) in THF (50 mL) at 0° C. was added 1-(benzyloxy)-2-methylpropan-2-ol (9.36 g, 51.9 mmol) dropwise. After being stirred at room temperature for 0.5 h, 3-bromoprop-1-yne (12.4 g, 104 mmol) was added slowly at 0° C. The mixture was then stirred at reflux overnight. The reaction was quenched by addition of sat. NH4Cl. The resulting mixture was extracted with ethyl acetate (30 mL×3). The organic layer was combined, dried over with Na2SO4, and concentrated. The residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (20/1) to afford the title compound (9.72 g, 86%) as pale yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.34-7.35 (m, 5H), 4.56 (s, 2H), 4.18 (d, J=2.0 Hz, 2H), 3.38 (s, 2H), 2.34 (t, J=2.0 Hz, 1H), 1.25 (s, 6H).

Workup

  1. stirringThe mixture was then stirred
  2. temperatureat reflux overnight
  3. customThe reaction was quenched by addition of sat. NH4Cl
  4. extractionThe resulting mixture was extracted with ethyl acetate (30 mL×3)
  5. dry with materialdried over with Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with petroleum ether/ethyl acetate (20/1)

Sources & evidence

ORD record
ord-0017db3f93174796b5e97fa3dec6d346
Source dataset
uspto-grants-2015_12
Patent number
US09212186B2

Reaction notes

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