Diethyl Ether → HCID 22731324, compound

HRID 2085578Notes

Reaction equation

HRID 2085578 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]=[O:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1.[C:15]([Mg]Cl)([CH3:18])([CH3:17])[CH3:16].CCOCC>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:13]([OH:14])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 22731282HCID 22731282, compound2×HCID 178418310HCID 178418310, compound

Product 1

HCID 22731324HCID 22731324, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred, cooled (ice-bath) solution of 5-bromo-3,3-dimethyl-2,3-dihydrobenzofuran-7-carbaldehyde (Intermediate 30, 1.72 g, 6.74 mmol) in 15 mL of anhydrous tetrahydrofuran was treated with a 1M solution of tert-butyl magnesium chloride solution in ether (6.74 mL, 6.74 mmol). The reaction mixture was then allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated to an oil that on flash column chromatography using 5% ethyl acetate in hexane as the eluent afforded the title compound (0.95 g, 45%).

Workup

  1. washwashed with brine
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated to an oil that on flash column chromatography

Sources & evidence

ORD record
ord-5847721867084b0eaa451ab96a20c4d7
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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