Isopropanol → HCID 18364408, compound

HRID 380240Notes

Reaction equation

HRID 380240 reaction equation
[Cl:1][C:2]1[C:3]2[CH:13]=[C:12]3[O:14][CH2:15][O:16][C:11]3=[CH:10][C:4]=2[S:5][C:6]=1[C:7](O)=[O:8].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O)(C)C.[Cl-].[Na+]>O1CCCC1>[Cl:1][C:2]1[C:3]2[CH:13]=[C:12]3[O:14][CH2:15][O:16][C:11]3=[CH:10][C:4]=2[S:5][C:6]=1[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 5234Sodium ChlorideHCID 183643997-Chloro-2H-thieno[2,3-f][1,3]benzodioxole-6-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 18364408HCID 18364408, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.14 mol of the compound obtained in Step B is added at 5° C. under an inert atmosphere to a solution of 0.15 mol of LiAlH4 in 450 ml of tetrahydrofuran. After 2 hours' reaction at ambient temperature, the reaction mixture is hydrolysed by the addition of 85 ml of isopropanol and 31 ml of saturated sodium chloride solution. After stirring for 12 hours at ambient temperature, the reaction mixture is filtered over Celite. The organic phase is then concentrated under reduced pressure, taken up in dichloromethane and washed with water and then with saturated NaCl solution. After the organic phase has been dried over calcium sulphate, the solution is concentrated under reduced pressure, allowing the expected product to be obtained.

Workup

  1. customAfter 2 hours' reaction at ambient temperature
  2. filtrationthe reaction mixture is filtered over Celite
  3. concentrationThe organic phase is then concentrated under reduced pressure
  4. washwashed with water
  5. dry with materialAfter the organic phase has been dried over calcium sulphate
  6. concentrationthe solution is concentrated under reduced pressure
  7. customto be obtained

Sources & evidence

ORD record
ord-7d0a7e5a4db34cadae433ca78e14a679
Source dataset
uspto-grants-2001_10
Patent number
US06302837B1

Reaction notes

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