Water → HCID 10034910, compound

HRID 1612779Notes

Reaction equation

HRID 1612779 reaction equation
[H-].[Na+].[CH3:3][PH:4](=[O:8])[O:5][CH2:6][CH3:7].Br[CH2:10][CH:11]1[CH2:13][CH2:12]1.O>O1CCCC1>[CH:13]1([CH2:12][P:4]([CH3:3])(=[O:8])[O:5][CH2:6][CH3:7])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 178476777HCID 178476777, compound

Product 1

HCID 10034910HCID 10034910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2.22 g of sodium hydride (80% in oil) in 50 ml of anhydrous tetrahydrofuran under an inert atmosphere at 20° is treated with 50 ml of an anhydrous tetrahydrofuran solution of 7.24 g of ethyl (methyl)phosphinate at such a rate so that the temperature does not exceed 25°. After the addition is complete the resulting suspension is stirred for 1 hour at room temperature before slow addition of 10.0 g of bromomethylcyclopropane. The reaction mixture is stirred for a further 3 hours at 20° cooled in an ice/water bath and 100 ml of water added carefully. The clear solution is then partitioned between dichloromethane and water. Separation of the organic layer followed by drying and removal of the solvent affords a pale yellow oil. Distillation under high vacuum affords ethyl cyclopropylmethyl(methyl)phosphinate of b.p. 100° C. (10-1 mbar); 1H-NMR (CDCl3): δ (ppm)=4.04 (2H, m, CH2OP) 1.66 (2H, d, CH2P), 1.47 (3H, d, CH3), 1.30 (3H, t, CH3) 0.88 (1H, m, CH), 0.55 (2H, m, CH2), 0.15 (2H, m, CH2).

Workup

  1. customdoes not exceed 25°
  2. additionAfter the addition
  3. temperaturecooled in an ice/water bath
  4. customThe clear solution is then partitioned between dichloromethane and water
  5. customSeparation of the organic layer
  6. customby drying
  7. customremoval of the solvent
  8. customaffords a pale yellow oil
  9. distillationDistillation under high vacuum

Sources & evidence

ORD record
ord-9a727975b91c4804861331f19cf1d10f
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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