Tetrahydrofuran → Methyl(4-cyclopropyl-6-hydroxy-1-benzothiophen-3-yl)acetate

HRID 591507Notes

Reaction equation

HRID 591507 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[C:9]2[C:10]([CH:25]3[CH2:27][CH2:26]3)=[CH:11][C:12]([O:14][Si](C(C)C)(C(C)C)C(C)C)=[CH:13][C:8]=2[S:7][CH:6]=1.C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[C:9]2[C:10]([CH:25]3[CH2:27][CH2:26]3)=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 131734522Methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate

Product 1

HCID 131734523Methyl(4-cyclopropyl-6-hydroxy-1-benzothiophen-3-yl)acetateYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl(4-cyclopropyl-6-((triisopropylsilyl)oxy)-1-benzothiophen-3-yl)acetate (372 mg) and THF (2 mL) was added TBAF (1M in THF, 1.333 mL) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (201 mg).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-318f2eea7f5b440bb2f7ca5234f14ab0
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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