Homoallyl bromide → HCID 12045755, compound

HRID 392569Notes

Reaction equation

HRID 392569 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[H-].[Na+].Br[CH2:16][CH2:17][CH:18]=[CH2:19]>CN(C=O)C.C(Cl)Cl>[CH2:16]([C:7]1([CH2:10][CH2:11][CH:3]=[CH2:4])[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:8]1=[O:12])[CH2:17][CH:18]=[CH2:19]

Participants

6

Reactant 3

HCID 21241Homoallyl bromideHCID 24758Sodium hydrideHCID 787875-Methoxyindan-1-one

Product 1

HCID 12045755HCID 12045755, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxy-1-indanone (1 g, 6.17 mmol) in DMF (6 mL) at rt was added NaH (740 mg, 61% in oil, 18.5 mmol) and 4-bromo-1-butene (2.5 mL, 24.7 mmol). After 20 h at rt, the solution was diluted with CH2Cl2 and quenched with saturated aqueous NH4Cl. The slurry was dried with MgSO4 and filtered through a plug of silica and rinsed with 10% EtOAc in hexanes. The filtrate was concentrated and provided crude 2,2-di(3-butenyl)-5-methoxy-1-indanone.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. dry with materialThe slurry was dried with MgSO4
  3. filtrationfiltered through a plug of silica
  4. washrinsed with 10% EtOAc in hexanes
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-082eab2f9fbe43bdb30ea1095ed79018
Source dataset
uspto-grants-2004_10
Patent number
US06800785B1

Reaction notes

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