Ethyl Acetate → HCID 67804591, compound

HRID 704612Notes

Reaction equation

HRID 704612 reaction equation
Br[Si](C)(C)C.[CH:6]1(/[CH:12]=[C:13](\[CH2:27][P:28]([O:34]CC)([CH2:30][CH:31]([CH3:33])[CH3:32])=[O:29])/[C:14]([O:16][CH:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:19](=[O:20])[O:18]2)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(OCC)(=O)C.[Cl-].[NH4+]>ClCCl.ClCCl.CO.C(O)(=O)C>[CH:6]1(/[CH:12]=[C:13](\[CH2:27][P:28]([OH:34])([CH2:30][CH:31]([CH3:32])[CH3:33])=[O:29])/[C:14]([O:16][CH:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:19](=[O:20])[O:18]2)=[O:15])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium Chloride2×HCID 76113BromotrimethylsilaneHCID 131716766HCID 131716766, compound

Product 1

HCID 67804591HCID 67804591, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21877243DCM MeOH AcOHSolvent

Procedure

Under an atmosphere of argon, 29 μl (0.22 millimole) of bromotrimethylsilane was added to a solution of 48 mg (0.11 millimole) of phthalidyl (Z)-3-cyclohexyl-2-(ethoxyisobutylphosphinoyl)methylpropenoate in 0.50 ml of dry dichloromethane, and the mixture was stirred at room temperature for 18 hours. To the reaction mixture were added 2.0 ml of ethyl acetate and 3.0 ml of a saturated aqueous solution of ammonium chloride, and the mixture was stirred at room temperature for 30 minutes. A saturated aqueous solution of ammonium chloride (3 ml) was added to the reaction mixture, and the mixture was extracted three times with 8 ml of ethyl acetate each time. The combined organic layers were dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography [silica gel 60 F254 made by E. Merck & Co.; dichloromethane/methanol/acetic acid (30:1:1)]to give 16 mg (yield 35%) of the captioned compound as a colorless oil. On standing, this compound solidified.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionthe mixture was extracted three times with 8 ml of ethyl acetate each time
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by preparative thin-layer chromatography [silica gel 60 F254

Sources & evidence

ORD record
ord-008f739e991b4721b343c6d2581cd1d3
Source dataset
uspto-grants-1991_01
Patent number
US04988681

Reaction notes

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