Diethyl chlorophosphate → HCID 67158781, compound

HRID 1891997Notes

Reaction equation

HRID 1891997 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2([CH3:23])[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]2[C:19]([O:21][CH3:22])=[O:20])[CH:7]=[CH:8][C:9]=1[Cl:10].[P:24](Cl)([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[O:25].[Cl-].[NH4+]>C(OCC)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2([CH3:23])[C:12]([C:19]([O:21][CH3:22])=[O:20])=[C:13]([O:18][P:24]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[O:25])[CH2:14][CH:15]([CH3:17])[CH2:16]2)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

6

Reactant 4

HCID 13139Diethyl chlorophosphateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67158461HCID 67158461, compound

Product 1

HCID 67158781HCID 67158781, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A stirred suspension of sodium hydride (60% in mineral oil, 13 mg) in diethyl ether (2 mL) was treated at rt with methyl (2RS,4RS)-2-(3,4-dichlorophenyl)-2,4-dimethyl-6-oxocyclohexanecarboxylate (100 mg). The mixture was stirred for 10 min and then a solution of diethyl chlorophosphate in diethyl ether (2 mL) was added. Upon completion of addition, the resulting mixture was stirred at rt for 3 h. After this time, solid ammonium chloride was added and stirring was continued for an additional 30 min. At the conclusion of this period, the resulting suspension was filtered through Celite and the filtrate was concentrated under vacuum to provide methyl (4RS,6SR)-6-(3,4-dichlorophenyl)-2-(diethoxyphosphoryloxy)-4,6-dimethyl-cyclohexen-1-carboxylate in quantitative yield. Mass spectrum m/z 465.19 (M+H+).

Workup

  1. additionUpon completion of addition
  2. stirringthe resulting mixture was stirred at rt for 3 h
  3. stirringstirring
  4. waitwas continued for an additional 30 min
  5. filtrationAt the conclusion of this period, the resulting suspension was filtered through Celite
  6. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-8321e6e426d740cfb1ab35d24ddbf7eb
Source dataset
uspto-grants-2013_08
Patent number
US08507559B2

Reaction notes

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