Water → HCID 55139138, compound

HRID 2400559Notes

Reaction equation

HRID 2400559 reaction equation
O[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10](=[O:13])([O-])[O-].[Cs+].[Cs+].BrC[CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.O>CN(C=O)C>[O:21]1[CH2:22][CH2:23][CH:18]([O:13][CH2:10][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 130194-CyanophenolHCID 27732864-(Bromomethyl)oxane

Product 1

HCID 55139138HCID 55139138, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-hydroxybenzonitrile (665 mg, 5.59 mmol) and caesium carbonate (2.00 g, 6.14 mmol) in DMF (5 mL) was added 4-(bromomethyl)tetrahydro-2H-pyran (1.00 g, 5.59 mmol), and the reaction mixture was stirred at 80° C. over night. After cooling to rt, the reaction mixture was poured into water. After stirring for a few minutes, the precipitate was collected by filtration, washed with water and dried in vacuo to give the title compound (785 mg, 65%): 1H NMR (400 MHz, CDCl3) δ 7.58 (d, 2H), 7.92 (d, 2H), 4.05-4.00 (dd, 2H), 3.82 (d, 2H), 3.48-3.41 (m, 2H), 2.15-2.02 (m, 1H), 1.78-1.72 (dd, 2H), 1.52-1.41 (m, 2H); ES-MS m/z 218, HPLC RT (Method D) 2.09 min.

Workup

  1. temperatureAfter cooling to rt
  2. stirringAfter stirring for a few minutes
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a1d52a7370414af091695399f40e04c2
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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