Allyl bromide → HCID 69890792, compound

HRID 2119703Notes

Reaction equation

HRID 2119703 reaction equation
[C:1]([C:5]1[C:19]([OH:20])=[CH:18][C:8]2[CH2:9][C:10]3([O:17][C:7]=2[CH:6]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:23](Br)[CH:24]=[CH2:25].[Cl-].[NH4+]>CN(C)C=O>[C:1]([C:5]1[C:19]([O:20][CH2:25][CH:24]=[CH2:23])=[CH:18][C:8]2[CH2:9][C:10]3([O:17][C:7]=2[CH:6]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 12094374HCID 12094374, compound

Product 1

HCID 69890792HCID 69890792, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen stream, a solution of 0.76 g of 6-t-butyl-5-hydroxy-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane synthesized in Example 7 in 6 ml of dimethylformamide was added dropwise to a suspension of 0.13 g of oily sodium hydride in 6 ml of dimethylformamide at 0° C. After stirring for 30 minutes, 0.28 ml of allyl bromide was added dropwise and the mixture was stirred overnight and allowed to attain room temperature. The reaction mixture was poured into a saturated aqueous ammonium chloride solution and extracted with n-hexane. The organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 1%-2% ethyl acetate) to give 0.76 g of 6-t-butyl-5-(2-propenyloxy)-2,3-dihydrobenzofuran-2-spiro-1′-cycloheptane as a colorless oil (yield 90%).

Workup

  1. stirringthe mixture was stirred overnight
  2. customto attain room temperature
  3. extractionextracted with n-hexane
  4. washThe organic layers were washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 1%-2% ethyl acetate)

Sources & evidence

ORD record
ord-d4620e166b1943db9d598571da5aabed
Source dataset
uspto-grants-2004_02
Patent number
US06686389B2

Reaction notes

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