HCID 22664994, compound → HCID 22664990, compound

HRID 392572Notes

Reaction equation

HRID 392572 reaction equation
[CH2:1]([C:5]1([CH2:19][CH2:20][CH2:21][CH:22]=[CH2:23])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH2:15][O:16][CH3:17])[CH:11]=2)[C:6]1=[O:18])[CH2:2][CH2:3][CH3:4].[CH2:24]([Mg]Br)[CH:25]=[CH2:26]>O1CCCC1>[CH2:1]([C:5]1([CH2:19][CH2:20][CH2:21][CH:22]=[CH2:23])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH2:15][O:16][CH3:17])[CH:11]=2)[C:6]1([C:25]([CH3:26])=[CH2:24])[OH:18])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 22664994HCID 22664994, compoundHCID 178455850HCID 178455850, compound2×

Product 1

HCID 22664990HCID 22664990, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-butyl-5-(methoxymethoxy)-2-(4-pentenyl)-1-indanone (400 mg, 1.27 mmol) in anhydrous tetrahydrofuran (THF, 5 mL) was placed under a N2 atmosphere, cooled in a dry ice-acetone bath, stirred, and treated with 2-propenyl magnesium bromide, (1M in THF, 1.9 mL, 1.9 mmol). After warming to room temperature, the mixture was treated with additional 2-propenyl magnesium bromide (1M in THF, 6 mL, 6 mmol) and stirred at room temperature overnight. The mixture was quenched with saturated aqueous NH4Cl, dried over MgSO4, filtered through a pad of silica, and concentrated under vacuum to afford an oil. The crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4.0×7.0 cm) silica gel column, eluting with 19:1 hexanes-EtOAc. The product-containing fractions were evaporated under vacuum to afford 2-butyl-1-isopropenyl-5-(methoxymethoxy)-2-(4-pentenyl)-1-indanol as an oil.

Workup

  1. temperaturecooled in a dry ice-acetone bath
  2. stirringstirred at room temperature overnight
  3. customThe mixture was quenched with saturated aqueous NH4Cl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through a pad of silica
  6. concentrationconcentrated under vacuum
  7. customto afford an oil
  8. customThe crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4.0×7.0 cm) silica gel column
  9. washeluting with 19:1 hexanes-EtOAc
  10. customThe product-containing fractions were evaporated under vacuum

Sources & evidence

ORD record
ord-a3ead8cf92d94f728d70e871050a6945
Source dataset
uspto-grants-2004_10
Patent number
US06800785B1

Reaction notes

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