Sodium hydride → HCID 12045756, compound

HRID 392570Notes

Reaction equation

HRID 392570 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][CH2:18][CH:19]=[CH2:20]>CN(C=O)C.C(Cl)Cl>[CH2:16]([C:7]1([CH2:5][CH2:4][CH2:3][CH:11]=[CH2:10])[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][CH2:18][CH:19]=[CH2:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 707041-Pentene, 5-bromo-HCID 787875-Methoxyindan-1-one

Product 1

HCID 12045756HCID 12045756, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxy-1-indanone (2.5 g, 15.4 mmol) in DMF (20 mL) at rt was added NaH (1.8 g, 61% in oil, 46.2 mmol) and 5-bromo-1-pentene (5.48 mL, 46.2 mmol). After 6 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(4-pentenyl)-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-9f4570ca36b4458788694475b6af93ba
Source dataset
uspto-grants-2004_10
Patent number
US06800785B1

Reaction notes

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