Acetonitrile → HCID 86695792, compound

HRID 922316Notes

Reaction equation

HRID 922316 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][P:10](=[O:15])([O:13]C)[O:11][CH3:12])=[CH:4][CH:3]=1.[C:16]([O-])([O-])=O.[K+].[K+].Br[CH2:23][C:24]1[CH:39]=[CH:38][C:27]([O:28][CH2:29][C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:31])=[CH:26][CH:25]=1.[C:40](#N)[CH3:41]>>[O:31]=[C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:29][O:28][C:27]1[CH:38]=[CH:39][C:24]([CH2:23][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][P:10](=[O:15])([O:13][CH2:40][CH3:41])[O:11][CH2:12][CH3:16])=[CH:4][CH:3]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 20392440Dimethyl [2-(4-hydroxyphenyl)ethyl]phosphonateHCID 66685859HCID 66685859, compound

Product 1

HCID 86695792HCID 86695792, compoundYield 45.2%

Conditions

Temperature
80 °C

Procedure

To a 50 mL RB flask fitted with magnetic stirrer was charged 10 mL of acetonitrile. To the stirred solvent was added dimethyl [2-(4-hydroxyphenyl)ethyl]phosphonate (0.17 g, 0.66 mmol) and K2CO3 (0.27 g, 1.97 mmol). Then it was stirred for 5 min. 2-[4-(bromomethyl)phenoxy]-1-phenylethanone (0.2 g, 0.66 mmol) was added. Then RM heated 80° C. for 2 h. After completion of the reaction (reaction monitored by TLC), the RM was concentrated in vacuum to remove the acetonitrile. To the residue was then added 100 mL of water and extracted with ethyl acetate (30 mL×2). The organic layer was washed with saturated brine solution (20 mL), dried over anhydrous Na2SO4 and evaporated to dryness gave the titled compound (0.14 g, 45.2%); 1H NMR (300 MHz, DMSO-d6): δ 8.01-8.04 (d, 2H), 7.68-7.70 (t, 1H), 7.55-7.60 (d, 2H), 7.33-7.36 (d, 2H), 7.14-7.17 (d, 2H), 6.96-6.98 (d, 2H), 6.89-6.92 (d, 2H), 5.59 (s, 2H), 4.98 (s, 2H), 3.92-4.04 (m, 4H), 2.66-2.75 (m, 2H), 1.94-2.05 (m, 2H), 1.18-1.91 (m, 6H)

Workup

  1. customTo a 50 mL RB flask fitted with magnetic stirrer
  2. customAfter completion of the reaction (reaction monitored by TLC)
  3. concentrationthe RM was concentrated in vacuum
  4. customto remove the acetonitrile
  5. additionTo the residue was then added 100 mL of water
  6. extractionextracted with ethyl acetate (30 mL×2)
  7. washThe organic layer was washed with saturated brine solution (20 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-883b3b16d3b54021abc5b92499cc54f5
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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