Methanol → (2,3-Dihydro-benzo[b]thiophen-5-yl)-acetic acid methyl ester

HRID 546258Notes

Reaction equation

HRID 546258 reaction equation
[S:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[C:7]([CH2:10][C:11]([OH:13])=[O:12])[CH:8]=[CH:9][C:2]1=2.[CH3:14]O>Cl>[CH3:14][O:12][C:11](=[O:13])[CH2:10][C:7]1[CH:8]=[CH:9][C:2]2[S:1][CH2:5][CH2:4][C:3]=2[CH:6]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 13704382(2,3-Dihydro-benzo[b]thiophen-5-yl)-acetic acid

Product 1

HCID 67190969(2,3-Dihydro-benzo[b]thiophen-5-yl)-acetic acid methyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Conditions

Temperature
65 °C

Procedure

In a round bottom flask was placed (2,3-dihydro-benzo[b]thiophen-5-yl)-acetic acid (525 mg, 2.70 mmol), methanol (15 mL) and hydrochloric acid (2 drops). The reaction mixture was heated to 65° C. for 16 h. It was then concentrated in vacuo to remove the methanol, diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The organic layers were combined and washed with a saturated aqueous sodium bicarbonate solution (10 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to afford (2,3-dihydro-benzo[b]thiophen-5-yl)-acetic acid methyl ester (528 mg, 94%) as a yellow oil: ES-HRMS m/e calcd for C11H12O2S (M+H)+ 209.0631, observed 209.0631.

Workup

  1. customIn a round bottom flask was placed
  2. concentrationIt was then concentrated in vacuo
  3. customto remove the methanol
  4. additiondiluted with water (20 mL)
  5. extractionextracted with ethyl acetate (3×20 mL)
  6. washwashed with a saturated aqueous sodium bicarbonate solution (10 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfb5f58112324318ac55002a1b613c57
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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