Hydrochloric Acid → HCID 58696425, compound

HRID 1178558Notes

Reaction equation

HRID 1178558 reaction equation
[H-].[Na+].[O:3]=[C:4]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:5][C:6]([O:8][CH3:9])=[O:7].[P:14](Cl)([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15].[NH4+].[Cl-].Cl>CCOCC>[CH2:17]([O:16][P:14]([O:3]/[C:4](/[CH2:10][CH2:11][CH2:12][CH3:13])=[CH:5]\[C:6]([O:8][CH3:9])=[O:7])([O:19][CH2:20][CH3:21])=[O:15])[CH3:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 13139Diethyl chlorophosphateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 546075Methyl 3-oxoheptanoate

Product 1

HCID 58696425HCID 58696425, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To NaH (60% in mineral oil, 2.8 g, 70 mmol) suspension in ether at 0° C. was added methyl 3-oxoheptanoate (10 g, 63 mmol) in anhydrous ether (50 mL) dropwise under Ar. The reaction mixture was stirred for 30 minutes. Diethyl chlorophosphate (9.6 mL, 67 mmol) was added dropwise under Ar at 0° C. The reaction mixture was stirred overnight allowing warm to room temperature. Saturated aqueous NH4Cl (22 mL) was added to quench the reaction. The mixture was then acidified with 1.0 N HCl. After separation, organic phase was washed with saturated aqueous NaHCO3, brine, dried (Na2SO4), filtered, concentrated. After column purification (silica gel, 1:1 EtOAc/Hexanes), the product was obtained as a colorless oil (17 g, 91%). 1HNMR (CDCl3) δ 0.89˜0.93 (m, 3H), 1.30˜1.45 (m, 3M), 1.50˜1.60 (m, 2H), 2.42 (m, 2H), 3.68 (s, 3H), 4.20˜4.35 (m, 4H), 5.35 (s, 1H).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. customto quench
  3. customthe reaction
  4. customAfter separation, organic phase
  5. washwas washed with saturated aqueous NaHCO3, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customAfter column purification (silica gel, 1:1 EtOAc/Hexanes)

Sources & evidence

ORD record
ord-2722857581434e97a8555efec86a6d83
Source dataset
uspto-grants-2007_10
Patent number
US07276531B2

Reaction notes

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