Ammonium Chloride → HCID 86691706, compound

HRID 921001Notes

Reaction equation

HRID 921001 reaction equation
[CH2:1]([Li])[CH2:2]CC.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].[NH4+].[Cl-]>C1COCC1>[CH3:23][O:22][C:20]1[CH:19]=[C:10]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([OH:12])[C:1]#[CH:2])[CH:9]=[C:8]([O:7][CH3:6])[CH:21]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 24261623HCID 24261623, compoundHCID 178418339Butyllithium

Product 1

HCID 86691706HCID 86691706, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

The following method was adapted from a literature procedure.vii Anhydrous THF (50 mL) was cooled to −78° C. Purified acetylene gas was gently bubbled through the THF for 1 hour. A 2.5M solution of n-butyllithium in THF (8.2 mL, 20.5 mmol) was then added drop-wise and the mixture was stirred vigorously for 20 minutes. 3,5-Dimethoxybenzophenone (5.0 g, 20.5 mmol) was dissolved in 10 mL of anhydrous THF and the solution was slowly dropped into the reaction flask. The mixture was stirred vigorously for 20 minutes at −78° C. before being allowed to slowly warm to room temperature. A 5% aqueous solution of NH4Cl (60 mL) was added and the mixture stirred for 30 minutes. The product was extracted with ether (3×100 mL) and the combined organic layers were washed with brine (100 mL) and water (75 mL) before being dried with anhydrous magnesium sulfate. The filtrate was dried in vacuo to afford 1-(3,5-dimethoxyphenyl)-1-phenylprop-2-yn-1-ol as a yellow oil in 95% yield. 1H NMR (CDCl3): δ 7.62 (d, 3JH-H=7.2 Hz, 2H), 7.33 (t, 3JH-H=6.4 Hz, 2H), 7.29 (d, 3JH-H=7.2 Hz, 1H), 6.79 (d, 3JH-H=2.4 Hz, 2H), 6.37 (t, 3JH-H=2.4 Hz, 2H), 3.76 (s, 6H), 3.16 (s, 1H), 2.85 (s, 1H). 13C{1H} NMR (CDCl3): δ 160.68, 146.99, 144.35, 128.39, 127.99, 126.03, 104.60, 99.84, 86.45 (C2), 75.56 (C1), 74.33, 55.46. HR-MS (FAB+) Calculated for C17H17O3, 269.1172. found, 269.1178.

Workup

  1. customPurified acetylene gas was gently bubbled through the THF for 1 hour
  2. additionthe solution was slowly dropped into the reaction flask
  3. stirringThe mixture was stirred vigorously for 20 minutes at −78° C.
  4. temperatureto slowly warm to room temperature
  5. stirringthe mixture stirred for 30 minutes
  6. extractionThe product was extracted with ether (3×100 mL)
  7. washthe combined organic layers were washed with brine (100 mL) and water (75 mL)
  8. dry with materialbefore being dried with anhydrous magnesium sulfate
  9. customThe filtrate was dried in vacuo

Sources & evidence

ORD record
ord-7036bbd4afc4448abcd485dab88c4825
Source dataset
uspto-grants-2016_03
Patent number
US09273081B2

Reaction notes

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