Water → HCID 10262332, compound

HRID 1612773Notes

Reaction equation

HRID 1612773 reaction equation
[H-].[Na+].[CH:3]1([CH2:9][PH:10](=[O:14])[O:11][CH2:12][CH3:13])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:15]I.O>O1CCCC1>[CH:3]1([CH2:9][P:10]([CH3:15])(=[O:14])[O:11][CH2:12][CH3:13])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178476788HCID 178476788, compound

Product 1

HCID 10262332HCID 10262332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of 2.25 g of sodium hydride (55% dispersion in oil) in 10 ml of anhydrous tetrahydrofuran is cooled to 0° under an inert atmosphere. A solution of 8.9 g of ethyl (cyclohexylmethyl)phosphinate in 10 ml of anhydrous tetrahydrofuran is added dropwise maintaining the temperature at between 0°-5°. After the addition is complete the suspension is warmed to room temperature and stirred for 30 minutes before re-cooling to 0° C. A solution of 19.87 g of methyl iodide in 10 ml of anhydrous tetrahydrofuran is added slowly--very exothermic! After warming to room temperature, the reaction mixture is stirred for 45 minutes, re-cooled to 0° and carefully treated with water. Removal of the organic phase, drying and concentration affords a yellow oil. Chromatography on silica gel gives ethyl P-cyclohexylmethyl-P-methylphosphinate as a colourless oil; 1H-NMR (CDCl3): δ (ppm)=4.04 (2H, m, CH2OP), 1.94-1.57 (7H, m, 3×CH2 +CH), 1.45 (3H, d, J=15 Hz, P--CH3), 1.36-0.95 (9H, m, 3×CH2 +CH3).

Workup

  1. temperatureis cooled to 0° under an inert atmosphere
  2. temperaturemaintaining the temperature at between 0°-5°
  3. additionAfter the addition
  4. temperaturebefore re-cooling to 0° C
  5. temperatureAfter warming to room temperature
  6. stirringthe reaction mixture is stirred for 45 minutes
  7. temperaturere-cooled to 0°
  8. customRemoval of the organic phase
  9. customdrying
  10. concentrationconcentration
  11. customaffords a yellow oil

Sources & evidence

ORD record
ord-1f7237ad960645528d2932727e71524b
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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