Water → HCID 70855554, compound

HRID 591035Notes

Reaction equation

HRID 591035 reaction equation
[Br:1][C:2]1[C:3]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[C:7](O)=[O:8].[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].O>S(Cl)(Cl)=O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[CH2:7][OH:8]

Participants

6

Reactant 3

HCID 962WaterHCID 70855553HCID 70855553, compoundHCID 131720822Sodium tetraborohydride

Product 1

HCID 70855554HCID 70855554, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 3-bromo-4-methyl-benzo[b]thiophene-2-carboxylic acid (23c) (420 mg, 1.55 mmol) in thionyl chloride (10 mL) was refluxed for 1 hour. Thionyl chloride was then evaporated under reduced pressure and the residue was diluted with dimethoxyethane (20 mL). Sodium tetraborohydride (70 mg, 1.85 mmol) was then added to the solution. After 1 hour, the mixture was hydrolyzed with water (5 mL) and diluted with ethyl acetate (20 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated to dryness to afford the desired alcohol (23d) as a white solid without further purification (400 mg, 1.55 mmol, 100%).

Workup

  1. customThionyl chloride was then evaporated under reduced pressure
  2. additionthe residue was diluted with dimethoxyethane (20 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-4d3f119bc0c44eb9aa475daca1429abf
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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