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

HRID 1106695Notes

Reaction equation

HRID 1106695 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 with chloroform (5×), 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 with chloroform (5×)
  5. dry with materialthe combined organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bc1e4203af5b4694aca23db5944282d2
Source dataset
uspto-grants-2000_05
Patent number
US06057352

Reaction notes

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