Triethylamine → HCID 178476788, compound

HRID 1463646Notes

Reaction equation

HRID 1463646 reaction equation
[CH:1]1([CH2:7][PH:8](=[O:10])[O-:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:11](N(CC)CC)[CH3:12].C(OC(Cl)=O)C>O1CCCC1>[CH:1]1([CH2:7][PH:8](=[O:9])[O:10][CH2:11][CH3:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178527043HCID 178527043, compound

Product 1

HCID 178476788HCID 178476788, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

19.3 g of cyclohexylmethylphosphinate are is dissolved in 60 ml of absolute tetrahydrofuran under an inert atmosphere. The solution is cooled to 0° C. and a suspension forms which is treated with 12.14 g of triethylamine. An exothermic reaction occurs. The suspension is re-cooled to 0° C. before dropwise addition of 13.02 g of ethylchloroformate. A further exothermic reaction with gas-evolution is observed together with the formation of a white precipitate. The resulting suspension is warmed to 20° and stirred for 20 hours. The solid is removed by filtration and the filtrate is evaporated to dryness. The residue is dissolved in dichloromethane and washed with water. Drying and removal of the solvent affords a pale yellow oil. Distillation under high vacuum affords ethyl cyclohexylmethylphosphinate, b.p. 120°-130° C/2×10-1 mbar. 1H-NMR (CDCl3): δ (ppm)=7.17 (1H, d, t, 5=527 MZ, P-H), 4.13 (2H, m, CH2OP), 1.95-1.58 (7H, m, 3×CH2 +CH), 1.38-0.95 (6H, m, 3×CH2).

Workup

  1. customAn exothermic reaction
  2. customA further exothermic reaction with gas-evolution
  3. temperatureThe resulting suspension is warmed to 20°
  4. customThe solid is removed by filtration
  5. customthe filtrate is evaporated to dryness
  6. dissolutionThe residue is dissolved in dichloromethane
  7. washwashed with water
  8. customDrying
  9. customremoval of the solvent
  10. customaffords a pale yellow oil
  11. distillationDistillation under high vacuum

Sources & evidence

ORD record
ord-f2d950dc14da46828de47b959c21b5b8
Source dataset
uspto-grants-1994_04
Patent number
US05300679

Reaction notes

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