Water → HCID 68088978, compound

HRID 509541Notes

Reaction equation

HRID 509541 reaction equation
I[C@H:2]1[CH2:6][CH2:5][O:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([SH:20])=[CH:16][CH:15]=1.O>CN(C=O)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][C@@H:2]2[CH2:6][CH2:5][O:4][CH2:3]2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 51675150(3S)-3-Iodooxolane

Product 1

HCID 68088978HCID 68088978, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (3S)-3-iodotetrahydrofuran [prepared according to the method outline in US2006004018] (1.2 g, 6.061 mmol) and K2CO3 (1.675 g, 12.12 mmol) in DMF (12.00 mL) at ambient temperature was added 4-bromobenzenethiol (1.146 g, 6.061 mmol). The resulting suspension was stirred at this temperature overnight. Water was added and then the aqueous layer extracted with DCM (×3). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give the sub-title compound as a clear oil which was used directly in the next step without further purification.

Workup

  1. customprepared
  2. customat ambient temperature
  3. extractionthe aqueous layer extracted with DCM (×3)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb34729e4b884e34b2e979856ddefa28
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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