Sulfuric Acid → 5-Diethylphosphono-2-thiophenecarboxaldehyde

HRID 1431005Notes

Reaction equation

HRID 1431005 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[S:10][C:11]([CH:14]2N(C)CCN2C)=[CH:12][CH:13]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].S(=O)(=O)(O)[OH:22]>O>[CH2:6]([O:5][P:4]([C:9]1[S:10][C:11]([CH:14]=[O:22])=[CH:12][CH:13]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86659557[5-(1,3-Dimethyl-imidazolidin-2-yl)-thiophen-2-yl]-phosphonic acid diethyl ester

Product 1

HCID 222749525-Diethylphosphono-2-thiophenecarboxaldehydeYield 48.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of [5-(1,3-dimethyl-imidazolidin-2-yl)-thiophen-2-yl]-phosphonic acid diethyl ester (17.2 g, 60.17 mmol) in water (20 ml) was added sulfuric acid (3 ml) over 5 mins. The reaction was stirred at r.t. for 20 min, diluted with water, extracted with EtOAc. The organic layer was washed with sat. NaHCO3, dried over MgSO4, filtrated, concentrated, purified by Biotage (80% EtOAc) to give (5-formyl-thiophen-2-yl)-phosphonic acid diethyl ester (7.2 g, 48.3%). 1H NMR (300 MHz, DMSO-d6): δ 10.02 (d, J=2.4 Hz, 1H), 8.09 (m, 1H), 7.75 (m, 1H), 4.05 (m, 4H), 1.24 (m, 6H). LC-MS m/z=249.4 [C9H13O4PS+H]+.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with sat. NaHCO3
  3. dry with materialdried over MgSO4
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. custompurified by Biotage (80% EtOAc)

Sources & evidence

ORD record
ord-3d6befb08a0d4d87a810554f793458a6
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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