Water → 1-Cyclopentyl-2-(4-methoxy-phenylsulfanyl)-ethanone

HRID 858555Notes

Reaction equation

HRID 858555 reaction equation
Cl[CH2:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1.C(N(CC)CC)C.O>C1COCC1>[CH:5]1([C:3](=[O:4])[CH2:2][S:18][C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 127654-MethoxybenzenethiolHCID 124665772-Chloro-1-cyclopentylethanone

Product 1

HCID 587625451-Cyclopentyl-2-(4-methoxy-phenylsulfanyl)-ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The intermediate 2-Chloro-1-cyclopentyl-ethanone from Step 1 (1 g, 6.81 mmol), was combined with 4-methoxy-benzenethiol (1.05 g, 7.50 mmol), in THF (20 mL) and treated with Triethylamine (1.05 mL, 7.50 mmol). The mixture was stirred for 1 hour at room temperature then poured into water (50 mL) and extracted with EtOAc (2×50 mL). The organics were then washed with 0.5N HCl (2×50 mL), 2N NaOH (2×50 mL), water (2×50 mL) and brine (1×50 mL) the organics were dried over Na2SO4, filtered and concentrated. The residue was used without further purification (1.65 g, 97%).

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe organics were then washed with 0.5N HCl (2×50 mL), 2N NaOH (2×50 mL), water (2×50 mL) and brine (1×50 mL) the
  3. dry with materialorganics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was used without further purification (1.65 g, 97%)

Sources & evidence

ORD record
ord-58a46c1cac644d9cada4923c4b515c61
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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