Triisopropyl phosphite → HCID 86618280, compound

HRID 562406Notes

Reaction equation

HRID 562406 reaction equation
Br[CH2:2][CH:3]1[CH2:5][CH2:4]1.[P:6]([O:15]C(C)C)([O:11][CH:12]([CH3:14])[CH3:13])[O:7][CH:8]([CH3:10])[CH3:9]>C(OCC)(=O)C>[CH:8]([O:7][P:6]([CH2:2][CH:3]1[CH2:5][CH2:4]1)(=[O:15])[O:11][CH:12]([CH3:14])[CH3:13])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 8304Triisopropyl phosphiteHCID 81503Bromomethylcyclopropane

Product 1

HCID 86618280HCID 86618280, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
144 °C

Procedure

Bromomethyl-cyclopropane (26.00 g, 0.193 mol) was added to triisopropyl phosphite (35.9 mL, 0.30 mol) at ambient temperature, under a nitrogen atmosphere. The resulting solution was stirred and heated at reflux (144° C. bath temperature) overnight. The reaction mixture was allowed to cool to ambient temperature and then ethyl acetate (350 mL) was added. The solution was washed with saturated sodium bicarbonate (350 mL) and then with saturated brine (2×350 mL). The organic phase was dried with magnesium sulfate, filtered, and concentrated by rotary evaporation and then under high vacuum to yield 39.96 g of cyclopropylmethyl-phosphonic acid diisopropyl ester (0.182 mol, 94% yield) as a colorless oil. 1H NMR (400 MHz, DMSO) δ 4.63-4.54 (m, 2H); 1.67-1.60 (d of d, 2H) 1.27-1.24 (d of d, 12H); 0.85-0.75 (m, 1H); 0.52-0.46 (m, 2H); 0.21-0.16 (m, 2H); ESMS (m/z): (M+1)+ found, 221; (M+23)+ found, 243.

Workup

  1. temperatureheated
  2. temperatureto cool to ambient temperature
  3. washThe solution was washed with saturated sodium bicarbonate (350 mL)
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-4273cb5acdab4f6a8e0b0e350227a71c
Source dataset
uspto-grants-2011_11
Patent number
US08067395B2

Reaction notes

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