Butyl iodide → HCID 58604054, compound

HRID 2113670Notes

Reaction equation

HRID 2113670 reaction equation
[Cl:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]([F:14])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:7]2=[O:15].[H-].[Na+].I[CH2:24][CH2:25][CH2:26][CH3:27]>CN(C)C=O>[CH2:24]([C:6]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:5][CH2:4][C:3]2[C:8](=[CH:9][C:10]([F:14])=[C:11]([O:12][CH3:13])[C:2]=2[Cl:1])[C:7]1=[O:15])[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 58604075HCID 58604075, compound

Product 1

HCID 58604054HCID 58604054, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-chloro-7-fluoro-6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate (651 mg, 2.17 mmol) was dissolved in dimethylformamide (DMF, 2.2 mL) with gentle heating. After cooling to room temperature, sodium hydride (160 mg, 61% dispersion in mineral oil, 4.0 mmol) was added to give a black solution which was placed under N2. Iodobutane (1.15 mL, 10 mmol) was added and the reaction stirred at room temperature for 19 hours. The reaction mixture was then partitioned between EtOAc/H2O and the organic portion was washed with brine, dried over MgSO4, filtered and evaporated under vacuum. The crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7.5 cm) silica gel column, eluting with 1000 mL of 2% EtOAc in hexane. The product-containing fractions were concentrated to give ethyl 2-butyl-5-chloro-7-fluoro-6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate.

Workup

  1. customto give a black solution which
  2. customThe reaction mixture was then partitioned between EtOAc/H2O
  3. washthe organic portion was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe crude product was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7.5 cm) silica gel column
  8. washeluting with 1000 mL of 2% EtOAc in hexane
  9. concentrationThe product-containing fractions were concentrated

Sources & evidence

ORD record
ord-c17f3b21d68342c48436ac4eb14412b3
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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