Water → 5-(3-Hydroxypropyl)thiophene-2-carbaldehyde

HRID 629156Notes

Reaction equation

HRID 629156 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[S:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.O>CO.O>[OH:8][CH2:9][CH2:10][CH2:11][C:12]1[S:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 962WaterHCID 1317353645-(3-((t-Butyldimethylsilyl)oxy)propyl)thiophene-2-carbaldehyde

Product 1

HCID 1182289755-(3-Hydroxypropyl)thiophene-2-carbaldehydeYield 69.1%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of crude 5-(3-((t-butyldimethylsilyl)oxy)propyl)thiophene-2-carbaldehyde (ca. 871 mg, 3.06 mmol) in 32 mL of 9:1 methanol/water was added p-tosic acid monohydrate (58 mg, 0.31 mmol). The resulting mixture was stirred at room temperature for 45 minutes and poured into 100 mL water. Organics were extracted with ethyl acetate (2×75 mL) and ether (75 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (20-50% ethyl acetate in hexanes) to give 5-(3-hydroxypropyl)thiophene-2-carbaldehyde (360 mg, 69%).

Workup

  1. extractionOrganics were extracted with ethyl acetate (2×75 mL) and ether (75 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washThe crude residue was subjected to chromatography on silica gel with gradient elution (20-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1b965ab890a24ebeb1e138baa8a4fc3e
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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