Tetrahydrofuran → HCID 59167802, compound

HRID 1616591Notes

Reaction equation

HRID 1616591 reaction equation
C1COCC1.[CH3:6][O:7][C:8](=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[S:15])[NH2:14].Br[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[OH:29])=O>CCOC(C)=O>[CH3:6][O:7][C:8](=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[S:15][CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[OH:29])[N:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11265069HCID 11265069, compoundHCID 23254886HCID 23254886, compound

Product 1

HCID 59167802HCID 59167802, compoundYield 165.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Add THF (50 mL, anhydrous) to a roundbottom flask containing 5-thiocarbamoyl-pentanoic acid methyl ester (2.63 g, 15.0 mmol) and 2-bromo-1-(2-hydroxy-4-methoxy-phenyl)-ethanone (4.90 g, 15.0 mmol, 75% pure). Heat to reflux under N2 overnight. Cool to room temperature, add EtOAc, wash with saturated NaHCO3 solution, brine, and backextract from each aqueous layer with EtOAc. Dry combined organic layers over MgSO4 and concentrate to get 8 grams of a yellow solid. Adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 0-20% EtOAc/hexanes followed by flash chromatography on silica gel eluting with CHCl3 to afford the title compound (2.69 g, 56%). MS (IS) 322 (M+1)+.

Workup

  1. temperatureHeat
  2. temperatureto reflux under N2 overnight
  3. washwash with saturated NaHCO3 solution, brine, and backextract from each aqueous layer with EtOAc
  4. customDry
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-15fa3900f9954acfb4247c30df9d3741
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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