HCID 21850811, compound → HCID 178454802, compound

HRID 1720871Notes

Reaction equation

HRID 1720871 reaction equation
[OH:1][C:2]([PH:5](=[O:8])[O:6][CH3:7])([CH3:4])[CH3:3].O[C:10](P(O)O)([CH3:12])[CH3:11]>O>[OH:1][C:2]([PH:5](=[O:8])[O:6][CH2:7][CH:10]([CH3:12])[CH3:11])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 21850811HCID 21850811, compoundHCID 178502930HCID 178502930, compound

Product 1

HCID 178454802HCID 178454802, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

The methyl (1-hydroxy-1-methylethyl)phosphinate prepared as described immediately above is heated with water (11) on a steam bath for 8 hours until conversion to 1-hydroxy-1-methylethylphosphonous acid is complete (monitored by 31P nmr). The water is removed on a rotary evaporator and the residue is completely dried by co-evaporation with toluene. A sample of this phosphonous acid (4.6 g, 0.037M), isobutyl alcohol (3.02 g, 0.041M) and dimethylaminopyridine (0.5 g, 0.0041M) is stirred at 5° C. in tetrahydrofuran. Dicyclohexylcarbodiimide (8.4 g, 0.041M) is added portionwise over 30 minutes. On completion of the reaction (31P nmr), ether (50 ml) is added and the precipitated dicyclohexyl urea is filtered off.

Workup

  1. customThe water is removed on a rotary evaporator
  2. dry with materialthe residue is completely dried by co-evaporation with toluene
  3. additionDicyclohexylcarbodiimide (8.4 g, 0.041M) is added portionwise over 30 minutes
  4. customOn completion of the reaction (31P nmr), ether (50 ml)
  5. additionis added
  6. filtrationthe precipitated dicyclohexyl urea is filtered off

Sources & evidence

ORD record
ord-525be789c6be45dcac34c541928c9e27
Source dataset
uspto-grants-1996_04
Patent number
US05508270

Reaction notes

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