Sodium Sulfite → Acetic acid, chloro(diethoxyphosphinyl)-, 1,1-dimethylethyl ester

HRID 1870540Notes

Reaction equation

HRID 1870540 reaction equation
[Cl:1][C:2](Cl)([P:10]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])=[O:11])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].S([O-])([O-])=O.[Na+].[Na+]>C(O)C.O>[Cl:1][CH:2]([P:10]([O:15][CH2:16][CH3:17])([O:12][CH2:13][CH3:14])=[O:11])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 24437Sodium SulfiteHCID 53950305HCID 53950305, compound

Product 1

HCID 10902235Acetic acid, chloro(diethoxyphosphinyl)-, 1,1-dimethylethyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

The title compound of Step B (18.4 g, 0.0572 mol) was dissolved in ethanol (140 mL) and cooled to 0° C. A solution of sodium sulfite (14.4 g, 0.1144 mol) in H2O (63 mL) was added with stirring such that the internal temperature remained below 14° C. The cooling bath was removed and the mixture was stirred at room temperature for 30 min. The reaction mixture was extracted five times with chloroform, and the combined organic phase was dried (MgSO4), filtered and concentrated to afford 16.4 g of the title compound of Step C as a clear oil. 1H NMR (300 MHz, CDCl3): δ 4.43 (d,1H, J=15.9 Hz), 4.30-4.24 (m,4H), 1.52 (s,9H), 1.38 (t,6H, J=6.9 Hz).

Workup

  1. customremained below 14° C
  2. customThe cooling bath was removed
  3. stirringthe mixture was stirred at room temperature for 30 min
  4. extractionThe reaction mixture was extracted five times with chloroform
  5. dry with materialthe combined organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4144914206334a05b7c7cd5a3e7488e6
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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