Triethylamine → HCID 178476788, compound

HRID 1612772Notes

Reaction equation

HRID 1612772 reaction equation
[CH:1]1([CH2:7][P:8]([OH:10])[OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:11](N(CC)CC)[CH3:12].ClC(OCC)=O>O1CCCC1>[CH:1]1([CH2:7][PH:8](=[O:10])[O:9][CH2:11][CH3:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 19776469HCID 19776469, compound

Product 1

HCID 178476788HCID 178476788, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran solution of 19.3 g of cyclohexylmethylphosphonous acid is cooled to 5°, at which temperature a suspension forms, and treated with 12.14 g of triethylamine. An exothermia ensues and the suspension is re-cooled to 5° before slow addition of 13.02 g ethyl chloroformate in 20 ml of anhydrous tetrahydrofuran. An exothermic reaction occurs with gas evolution. The white suspension is stirred overnight at room temperature and subsequently filtered. The filtrate is concentrated under reduced pressure and the residue partitioned between dichloromethane and water. The organic phase is removed, dried and concentrated in vacuo to give a yellow oil. Distillation in high vacuum affords ethyl (cyclohexylmethyl)phosphinate; b.p. 120°-130° (2×10-2 mbar); 1H-NMR (CDCl3): δ (ppm)=7.17 (1H, d, J=527 Hz, P--H), 4.13 (2H, m, CH2OP), 1.95-1.58 (7H, m, 3×CH2 +CH), 1.38-0.75 (9H, m, 3×CH2 +CH3).

Workup

  1. customAn exothermic reaction
  2. filtrationsubsequently filtered
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue partitioned between dichloromethane and water
  5. customThe organic phase is removed
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customto give a yellow oil
  9. distillationDistillation in high vacuum

Sources & evidence

ORD record
ord-70be2914d3ae48e082a304f3f51afce7
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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