Diethyl Ether → HCID 22731342, compound

HRID 2085585Notes

Reaction equation

HRID 2085585 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(OCC)C.[CH:20]1([Mg]Cl)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(OCC)(=O)C>CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:13]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[OH:14])[C:5]2[O:9][CH2:8][C:7]([CH3:11])([CH3:10])[C:6]=2[CH:12]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 8857Ethyl AcetateHCID 22731282HCID 22731282, compound2×HCID 178478990HCID 178478990, compound

Product 1

HCID 22731342HCID 22731342, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Following General Procedure K and using 5-bromo-3,3-dimethyl-2,3-dihydrobenzofuran-7-carbaldehyde (Intermediate 30, 0.765 g, 3 mmol), 10 mL of anhydrous diethyl ether, and a 2M solution of cyclohexyl magnesium chloride solution in ether (3 mL, 6 mmol) followed by flash column chromatography using 10% ethyl acetate in hexane, the title compound was obtained (0.62 g, 61%).

Sources & evidence

ORD record
ord-579feeb74c05425a9cb24a8acfc2e5b5
Source dataset
uspto-grants-2004_04
Patent number
US06720423B2

Reaction notes

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