Tetrahydrofuran → HCID 131734530, compound

HRID 591530Notes

Reaction equation

HRID 591530 reaction equation
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:17]=[CH:16][C:9]2[C@H:10]([CH2:13][CH2:14]O)[CH2:11][O:12][C:8]=2[CH:7]=1.C1COCC1.CS(Cl)(=O)=O.[C:33](=[S:36])([O-:35])[CH3:34].[K+]>CN(C=O)C.CCN(CC)CC>[C:33](=[O:35])([S:36][CH2:14][CH2:13][C@H:10]1[C:9]2[CH:16]=[CH:17][C:6]([O:5][CH2:4][C:3]3[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:2]=3[Cl:1])=[CH:7][C:8]=2[O:12][CH2:11]1)[CH3:34]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 23670855Potassium ethanethioateHCID 89767792HCID 89767792, compound

Product 1

HCID 131734530HCID 131734530, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanol (678 mg) and THF (dry) (20 mL) were added methanesulfonyl chloride (0.310 mL) and Et3N (0.279 mL). The mixture was stirred at room temperature for 30 min. And then DMF (dry) (20.00 mL) and potassium ethanethioate (228 mg) were added to the mixture. The volatiles (THF) were removed by evaporation. The resulting mixture was stirred at 70° C. for 2 h. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (570 mg).

Workup

  1. customThe volatiles (THF) were removed by evaporation
  2. stirringThe resulting mixture was stirred at 70° C. for 2 h
  3. additionThe mixture was poured into water
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed successively with water and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-dc23030cdd664d9092448964fe8fbee6
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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