Tetrahydrofuran → HCID 22504114, compound

HRID 1814289Notes

Reaction equation

HRID 1814289 reaction equation
CON(C)[C:4](=[O:17])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[CH3:16].[CH2:19]1COCC1>O>[CH3:16][C:7]1[CH:8]=[CH:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]=1[CH2:5][C:4](=[O:17])[CH3:19]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 22504022N-Methoxy-N,2-dimethyl-1-naphthaleneacetamide

Product 1

HCID 22504114HCID 22504114, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

N-methoxy-N-methyl-2-(2-methyl-naphthalen-1-yl)-acetamide (1.01 g, 4.16 mmol) was dissolved in freshly distilled THF (17 mL) in an argon-purged, round-bottom flask. The mixture was chilled to 0° C. and methyl magnesium bromide (2.08 mL of 3.0 M soln in Et2O, 6.23 mmol) was added via syringe. The reaction was stirred at 0° C. for 75 minutes. TLC analysis (silica, 20% acetone-hexanes) indicated complete consumption of the starting material. The reaction was carefully quenched with a mixture of AcOH (1 mL) in EtOAc (5 mL). The quenched reaction was diluted with H2O and extracted three times with EtOAc. The organic extracts were combined, washed with brine solution, dried over Na2SO4, filtered through celite, and concentrated. Purification by flash chromatography (SiO2, 20% EtOAc-hexane) gave 1-(2-methyl-naphthalen-1-yl)-propan-2-one (343 mg, 1.73 mmol) in 41% yield. MS (APCI) m/z 199.1 (M+H). 1H NMR (300 MHz) CDCl3 δ 7.85 (m, 2H), 7.72 (d, J=9.4 Hz, 1H), 7.47 (m, 2H), 7.36 (d, J=8.2 Hz, 1H), 4.18 (s, 2H), 2.51 (s, 3H), 2.10 (s, 3H).

Workup

  1. custompurged
  2. additionmethyl magnesium bromide (2.08 mL of 3.0 M soln in Et2O, 6.23 mmol) was added via syringe
  3. customconsumption of the starting material
  4. customThe reaction was carefully quenched with a mixture of AcOH (1 mL) in EtOAc (5 mL)
  5. customThe quenched reaction
  6. extractionextracted three times with EtOAc
  7. washwashed with brine solution
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered through celite
  10. concentrationconcentrated
  11. customPurification by flash chromatography (SiO2, 20% EtOAc-hexane)

Sources & evidence

ORD record
ord-4b52d15483e04081bd65b40a6e81ead3
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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