Ethyl Bromide → HCID 15390471, compound

HRID 342175Notes

Reaction equation

HRID 342175 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]>O.C1COCC1>[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, 0.11 mol) and bromoethane (0.2 ml) were added to a mixed solution of 1-bromo-2-(2-tetrahydropyranyloxymethyl)benzene (27.11 g, 0.10 mol) and THF (50 ml) under an atmosphere of nitrogen gas. The mixture was stirred at room temperature for 1 hour to prepare a Grignard reagent. The Grignard reagent was added dropwise to a mixed solution of diethyl oxalate (29.23 g, 0.20 mol) and THF (100 ml) cooled to -78° C. The mixture was stirred at -78° C. for 1 hour, water (150 ml) was added, and the mixture was extracted with ether (200 ml). The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain ethyl 2-oxo-2-[2-(2-tetrahydropyranyloxymethyl)phenyl]acetate (22.60 g, Yield: 77.3%) as a colorless oil.

Workup

  1. temperaturecooled to -78° C
  2. stirringThe mixture was stirred at -78° C. for 1 hour
  3. extractionthe mixture was extracted with ether (200 ml)
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-a179488eaeef4d83814be2f0d156d673
Source dataset
uspto-grants-1999_01
Patent number
US05856573

Reaction notes

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