Water → 4-(4-Chlorophenoxy)thieno[2,3-c]pyridine-2-methanol

HRID 1369619Notes

Reaction equation

HRID 1369619 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([C:16](OC)=[O:17])=[CH:15][C:8]=23)=[CH:4][CH:3]=1.[Cl-].[Cl-].[Ca+2].[BH4-].[Na+].O>C(O)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([CH2:16][OH:17])=[CH:15][C:8]=23)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 10892544Methyl 4-(4-chlorophenoxy)thieno[2,3-c]pyridine-2-carboxylate

Product 1

HCID 185162834-(4-Chlorophenoxy)thieno[2,3-c]pyridine-2-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 61A (254 mg, 0.793 mmol) in absolute ethanol (4 mL) was treated with anhydrous CaCl2 (177 mg, 1.59 mmol), stirred for 1 hour, cooled to 0° C., treated with NaBH4 (123 mg, 3.25 mmol), stirred at 0° C. for 4 hours and at room temperature for 18 hours, treated with water and extracted with dichloromethane. The extract was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified on silica gel with 30% ethyl acetate/hexane to provided the title compound.

Workup

  1. stirringstirred at 0° C. for 4 hours and at room temperature for 18 hours
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-160d68f35118463e8ad27ff530f42be5
Source dataset
uspto-grants-2003_06
Patent number
US06579882B2

Reaction notes

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