Hydrochloric Acid → HCID 24820476, compound

HRID 1191944Notes

Reaction equation

HRID 1191944 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH:11](O)[CH2:10][CH2:9]2.Cl>O1CCCC1.O>[CH2:9]1[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([C:2]3[S:1][CH:5]=[CH:4][N:3]=3)[CH:7]=2)[CH:11]=[CH:10]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 24820475HCID 24820475, compound

Product 1

HCID 24820476HCID 24820476, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(1,3-thiazol-2-yl)indan-1-ol (900.00 mg, 0.0041420 mol) in tetrahydrofuran (20.00 mL) was added a 1.0 M solution of hydrogen chloride in water (20.00 mL). The reaction mixture was heated to reflux overnight. After cooling down to room temperature, the reaction was quenched with 30 mL of 1 N NaOH aqueous solution. The organic layer was separated and the aqueous phase was extracted with EtOAc (3×30 mL). The combined extracts were washed with brine, dried over anhydrous MgSO4, filtered, and evaporated under reduced pressure to afford the desired product (381 mg, 46%). LC-MS [M+H]=200.2.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customthe reaction was quenched with 30 mL of 1 N NaOH aqueous solution
  4. customThe organic layer was separated
  5. extractionthe aqueous phase was extracted with EtOAc (3×30 mL)
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ec0a2b14688f4d89bd7ebe1046f282d4
Source dataset
uspto-grants-2014_03
Patent number
US08680104B2

Reaction notes

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