Ethyl Bromide → HCID 15390471, compound

HRID 428005Notes

Reaction equation

HRID 428005 reaction equation
[Mg].BrCC.Br[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1.[C:20](OCC)(=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>O1CCCC1.O>[O:26]=[C:20]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][O:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 6332Ethyl BromideHCID 7268Diethyl OxalateHCID 53150262-[(2-Bromophenyl)methoxy]oxaneHCID 5462224Magnesium

Product 1

HCID 15390471HCID 15390471, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium (2.67 g, 0.110 mol) and bromoethane (0.20 ml) were added to a solution of 1-bromo-2-(tetrahydropyran-2-yloxymethyl)benzene (27.11 g, 0.100 mol) in tetrahydrofuran (50 ml) under an atmosphere of nitrogen, and the mixture was stirred at room temperature for 1 hour to prepare a Grignard reagent. The Grignard reagent was added dropwise to a solution of diethyl oxalate (29.23 g, 0.200 mol) in tetrahydrofuran (100 ml) cooled to −78° C. After stirring for 1 hour at −78° C., water (150 ml) was added. The mixture was extracted with ether, dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1) to give the desired compound ethyl 2-oxo-2-[2-(tetrahydropyran-2-yloxymethyl)phenyl]acetate (22.60 g, 77.3%) as an oil.

Workup

  1. temperaturecooled to −78° C
  2. stirringAfter stirring for 1 hour at −78° C.
  3. extractionThe mixture was extracted with ether
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-0bca595008a04eea9e7a447cfc739633
Source dataset
uspto-grants-2001_11
Patent number
US06313150B1

Reaction notes

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