4-Hydroxybenzaldehyde → HCID 22406500, compound

HRID 1503628Notes

Reaction equation

HRID 1503628 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][P:18](=[O:27])([O:23][CH:24]([CH3:26])[CH3:25])[O:19][CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH:24]([O:23][P:18]([CH2:17][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)(=[O:27])[O:19][CH:20]([CH3:22])[CH3:21])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 4366885Diisopropyl bromomethylphosphonate

Product 1

HCID 22406500HCID 22406500, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-hydroxybenzaldehyde (152 mg, 1.25 mmol) in DMF (20 mL) was added potassium carbonate (223 mg, 1.62 mmol), followed by diisopropyl bromomethylphosphonate (484 mg, 1.87 mmol). The mixture was heating in DMF at 90° C. under stirring for 17 hours. After evaporation of DMF under reduced pressure, 100 mL of water were added and the mixture was extracted with ethyl acetate (3*200 mL). The organic phase was washed with brine (100 mL), dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate (5:5)) to give 98.2 mg of an oil (26% yield). 1H NMR (250 MHz, CDCl3): δ 1.33 (t, J=6.0 Hz, 12H), 4.25 (d, J=10.2 Hz, 2H), 4.82 (q, J=6.0 Hz, 2H), 7.05 (d, J=8.7 Hz, 2H), 7.81 (d, J=8.7 Hz, 2H), 9.87 (s, 1H). 13C NMR (126 MHz, CDCl3): δ 25.4 (dd, J=12.7; 3.4 Hz), 64.0 (d, J=171.0 Hz) 73.3 (d, J=6.2 Hz), 116.3, 132.2, 133.3, 164.8 (d, J=13.4 Hz), 192.0. 31P NMR (202 MHz, CDCl3): δ 16.0

Workup

  1. customAfter evaporation of DMF under reduced pressure, 100 mL of water
  2. additionwere added
  3. extractionthe mixture was extracted with ethyl acetate (3*200 mL)
  4. washThe organic phase was washed with brine (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate (5:5))

Sources & evidence

ORD record
ord-7c9dc684e5ab4cefb092307d6f14e1b3
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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