Propargyl bromide → HCID 85760031, compound

HRID 1803753Notes

Reaction equation

HRID 1803753 reaction equation
[C:1]1([OH:11])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:12](Br)[C:13]#[CH:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:14]([O:11][C:1]1[CH:2]=[CH:3][CH:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2)[C:13]#[CH:12]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 682585,6,7,8-Tetrahydro-1-naphthol

Product 1

HCID 85760031HCID 85760031, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5,6,7,8-Tetrahydronaphthalen-1-ol (Aldrich, 3.93 g, 26.5 mmol), propargyl bromide (80% in toluene, 3.9 ml, 35 mmol), and potassium carbonate (4.83 g, 35 mmol) were stirred together in acetonitrile (75 mL) for 6 days at ambient temperature. The solvent was removed under reduced pressure, and the residue taken into water and extracted with diethyl ether. The organic layers were combined, dried with magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.76 (m, 4H), 2.49 (t, J=2.37 Hz, 1H), 2.68 (t, J=5.59 Hz, 2H), 2.75 (t, J=5.59, 2H), 4.69 (d, J=2.37 Hz, 2H), 6.74 (dd, J=7.80, 3.73 Hz, 2H), 7.06 (t, J=7.80 Hz, 1H). MS (DCI) m/z 187.06 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with diethyl ether
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bf0dc030cad14edab3aa31f46bcefa19
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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