Ethyl Acetate → HCID 53922974, compound

HRID 890773Notes

Reaction equation

HRID 890773 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O:7][CH2:8][CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].CCOC(C)=O>CN(C=O)C>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][N:10]([CH2:9][CH2:8][O:7][C:6]1[CH:15]=[C:16]([Cl:18])[CH:17]=[C:4]([Cl:3])[CH:5]=1)[S:11]([CH3:14])(=[O:12])=[O:13])[CH3:30]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoateHCID 22246767HCID 22246767, compound

Product 1

HCID 53922974HCID 53922974, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of NaH (60% in oil, 338 mg, 8.45 mmol) in DMF (23 mL) was cooled to 0° C. followed by addition of N-[2-(3,5-dichloro-phenoxy)-ethyl]-methanesulfonamide (2.0 g, 7.04 mmol). The reaction was stirred at room temperature for 0.5 h and was cooled to 0° C. followed by addition of ethyl 7-bromoheptanoate (2.0 g, 8.45 mmol). The reaction was heated at 65° C. for 3 h and was cooled to room temperature. EtOAc was added and the organic solution was washed consecutively with 1N HCl, water, and brine. The organic solution was dried (MgSO4), filtered, and concentrated. Purification by flash chromatography (4:1 hexanes:EtOAc) provided the title compound (2.84 g). 1HNMR (400 MHz, CDCl3) δ 6.95 (m, 1H), 6.75 (m, 2H), 4.06 (m, 5H), 3.56 (t, 2H), 3.22 (t, 2H), 2.86 (s, 3H), 2.26 (t, 2H), 1.60 (m, 4H), 1.32 (m, 4H), 1.22 (t, 3H).

Workup

  1. temperaturewas cooled to 0° C.
  2. temperatureThe reaction was heated at 65° C. for 3 h
  3. temperaturewas cooled to room temperature
  4. washthe organic solution was washed consecutively with 1N HCl, water, and brine
  5. dry with materialThe organic solution was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (4:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-d5a07c679a5449d1be061e06caf7b3f2
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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