Allyl iodide → HCID 58604049, compound

HRID 2113672Notes

Reaction equation

HRID 2113672 reaction equation
[H-].[Na+].[CH2:3]([CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([F:20])=[C:12]([O:18][CH3:19])[C:13]=2[Cl:17])[C:8]1=[O:21])[CH2:4][CH2:5][CH3:6].[CH2:22](I)[CH:23]=[CH2:24]>>[CH2:24]([C:7]1([CH2:3][CH2:4][CH2:5][CH3:6])[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([F:20])=[C:12]([O:18][CH3:19])[C:13]=2[Cl:17])[C:8]1=[O:21])[CH:23]=[CH2:22]

Participants

4

Reactant 3

HCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 58604047HCID 58604047, compound

Product 1

HCID 58604049HCID 58604049, compound

Procedure

Sodium hydride (15 mg, 61% dispersion in mineral oil, 0.38 mmol) was placed in a flame dried flask, then washed with hexanes to remove mineral oil, and finally suspended in DMF (0.3 mL) under an atmosphere of N2. A solution of 2-butyl-5-chloro-7-fluoro-6-methoxy-3,4-dihydro-2H-naphthalen-1-one (54 mg in 0.2 mL DMF, 0.19 mmol) was added at room temperature to give a bright yellow reaction mixture. After five minutes, allyl iodide (0.055 mL, 0.6 mmol) was added. The reaction was stirred for 1.5 hours, then partitioned between EtOAc/H2O. The organic phase was washed twice with water, dried over MgSO4, filtered and then evaporated under vacuum. The crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.), developing with 10:1 hexane-EtOAc. The product band at Rf 0.45-0.55 was eluted with 5% MeOH in CH2Cl2 and concentrated under vacuum to give 2-allyl-2-butyl-5-chloro-7-fluoro-6-methoxy-3,4-dihydro-2H-naphthalen-1-one as an oil.

Workup

  1. customdried flask
  2. washwashed with hexanes
  3. customto remove mineral oil
  4. customto give a bright yellow reaction mixture
  5. custompartitioned between EtOAc/H2O
  6. washThe organic phase was washed twice with water
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under vacuum
  10. customThe crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate (Analtech, Newark, Del.)
  11. washThe product band at Rf 0.45-0.55 was eluted with 5% MeOH in CH2Cl2
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ec31b29fabee47eb8b0bdaa2aca3fa97
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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