Triethyl phosphite → HCID 57661169, compound

HRID 384593Notes

Reaction equation

HRID 384593 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:15])[C:11]([OH:14])([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[P:16]([O:23]CC)([O:20]CC)[O:17]CC.C[Si](Br)(C)C>ClCCl>[OH:14][C:11]([CH3:13])([CH3:12])[C:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][P:16](=[O:17])([OH:23])[OH:20])=[CH:5][CH:6]=1)=[O:15]

Participants

5

Reactant 3

HCID 31215Triethyl phosphiteHCID 76113BromotrimethylsilaneHCID 68861821HCID 68861821, compound

Product 1

HCID 57661169HCID 57661169, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
140 °C

Procedure

A mixture of 10 g of 1-[4-(2-bromoethyl)phenyl]-2-hydroxy-2-methylpropan-1-one (0.037 moles) and 6.7 g (0.041 mol) of triethyl phosphite is heated externally at 140° C. for 24 hours. The reaction mixture is distilled to give 12.1 g of 2-[4-(2-hydroxy-2-methylpropionyl)phenyl]ethyl}phosphonic acid dimethyl ester. The ester is dissolved in 50 ml of dichloromethane, and a solution of 6.2 g (0.0405 mol) of trimethylsilyl bromide in 10 ml of dichloromethane is added drop wise at room temperature. The reaction mixture is stirred overnight. The reaction mixture is concentrated, and methanol (200 ml) is added. The mixture is stirred at temperature for 24 hours, and then concentrated to give 5.0 g of the title compound, a yellow oil.

Workup

  1. distillationThe reaction mixture is distilled
  2. customto give 12.1 g of 2-[4-(2-hydroxy-2-methylpropionyl)phenyl]ethyl}phosphonic acid dimethyl ester
  3. concentrationThe reaction mixture is concentrated
  4. additionmethanol (200 ml) is added
  5. stirringThe mixture is stirred at temperature for 24 hours
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-678e085ed1874115896c22cdc43da5b1
Source dataset
uspto-grants-2013_02
Patent number
US08367743B2

Reaction notes

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