Diethyl Ether → HCID 12272816, compound

HRID 2249543Notes

Reaction equation

HRID 2249543 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[O:11]1[CH:15]=[CH:14][CH2:13][CH2:12]1.C(OCC)C>O1CCOCC1.O>[CH3:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][CH:15]=[C:14]2[CH2:13][CH2:12][OH:11]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 709342,3-Dihydrofuran

Product 1

HCID 12272816HCID 12272816, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a suspension of 4-methylphenylhydrazine hydrochloride (2.50 g, 15.7 mmol) in 1,4-dioxane (25 mL) and water (1.5 mL) was dropped neat 2,3-dihydrofuran (1.66 g, 23.6 mmol). After the addition, the mixture was heated at 95° C. for 4 hours. After cooling to room temperature, it was poured into ethyl ether, dried over magnesium sulfate, evaporated to dryness. Flash chromatography on silica gel provided 0.485 g (18%) of the title compound as a solid. 1H NMR (500 MHz, CDCl3) δ 7.95 (br, 1H), 7.41 (s, 1H), 7.27 (d, 1H), 7.05 (m, 2H), 3.90 (dd, 2H), 3.01 (t, 2H), 2.46 (s, 3H), 1.50 (t, br, 1H).

Workup

  1. additionAfter the addition
  2. temperatureAfter cooling to room temperature
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b66303e8ac3845b4958cca946bc275ec
Source dataset
uspto-grants-2008_01
Patent number
US07314886B2

Reaction notes

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