Ethyl Acetate → HCID 131729243, compound

HRID 553994Notes

Reaction equation

HRID 553994 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.[Si:10]([O:27][CH2:28][C@H:29]1[CH2:34][O:33][CH2:32][C:31](=[O:35])[N:30]1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[NH4+].C(OCC)(=O)C>C1COCC1>[Si:10]([O:27][CH2:28][C@H:29]([NH:30][C:36](=[O:37])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:34][O:33][CH2:32][C:31]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:35])([C:23]([CH3:26])([CH3:25])[CH3:24])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 67466160HCID 67466160, compoundHCID 178478191HCID 178478191, compound

Product 1

HCID 131729243HCID 131729243, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

4-Chlorophenylmagnesium bromide (1 M solution in diethyl ether, 3.44 mL) was added dropwise to a solution of tert-butyl (R)-3-(tert-butyldiphenylsilanyloxymethyl)-5-oxomorpholine-4-carboxylate (1.47 g) in THF (35 mL) at −50° C. over five minutes, and the reaction solution was stirred at −40° C. for one hour. A saturated ammonium chloride solution was added to the solution in small portions at −40° C., and the reaction solution was returned to room temperature. Ethyl acetate was added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to obtain 1.48 g of the title compound. The property value of the compound is as follows.

Workup

  1. customwas returned to room temperature
  2. customthe organic layer was separated
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-1cdb388fbece465bafd7515a4b05e48b
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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