Water → HCID 86657603, compound

HRID 1911719Notes

Reaction equation

HRID 1911719 reaction equation
[AlH4-].[Li+].[CH2:3]([P:5]([CH2:12][CH:13]([CH3:16])[CH:14]=[O:15])(=[O:11])[O:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:4].O>C(OCC)C>[CH2:3]([P:5]([CH2:12][CH:13]([CH3:16])[CH2:14][OH:15])(=[O:11])[O:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 28112Lithium aluminum hydrideHCID 86657604HCID 86657604, compound

Product 1

HCID 86657603HCID 86657603, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

At room temperature, 2.3 g (0.06 mol) of lithium aluminohydride in 100 ml of absolute diethyl ether in a three-neck flask equipped with stirrer, dropping funnel and high-performance condenser are, while continuously stirring, admixed with a solution of 22.0 g (0.1 mol) of butyl ethyl(2-methyl-2-formylethyl)phosphinate in 100 ml of diethyl ether added dropwise at such a rate that there is a moderate boil of the diethyl ether. On completion of the dropwise addition the reaction solution is refluxed for 1 hour and subsequently admixed with 1.8 g (0.1 mol) of water. The insoluble salts are filtered off. The solvent of the filtrate is removed in vacuo and the product is purified by chromatography to obtain 18.9 g (85% of theory) of butyl ethyl(2-methyl-3-hydroxypropyl)phosphinate as colorless oil.

Workup

  1. additionadded dropwise at such a rate that there
  2. additionOn completion of the dropwise addition the reaction solution
  3. temperatureis refluxed for 1 hour
  4. filtrationThe insoluble salts are filtered off
  5. customThe solvent of the filtrate is removed in vacuo
  6. customthe product is purified by chromatography

Sources & evidence

ORD record
ord-62785e42a81a4d87801f27caf1db4666
Source dataset
uspto-grants-2013_12
Patent number
US08604108B2

Reaction notes

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