Ethanol → HCID 58540128, compound

HRID 1907795Notes

Reaction equation

HRID 1907795 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:14][C:5]2[S:6][C:7]([C:9]([O:11]CC)=[O:10])=[CH:8][C:4]=2[C:3]1=[O:15].C1COCC1.C(O)C.[OH-].[Li+]>O>[CH3:1][C:2]1([CH3:16])[CH2:14][C:5]2[S:6][C:7]([C:9]([OH:11])=[O:10])=[CH:8][C:4]=2[C:3]1=[O:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58539987Ethyl 5,5-Dimethyl-4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate

Product 1

HCID 58540128HCID 58540128, compoundYield 106.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 8 (310 mg, 1.30 mmol), THF (2 mL) and ethanol (2 mL). A solution of lithium hydroxide (125 mg, 5.21 mmol) in water (2 mL) was added, and the mixture was stirred at 50° C. for 2 h. After this time, the organic solvents were removed under reduced pressure, water (6 mL) was added, and the pH was adjusted to 3.0 with 2 N hydrochloric acid. The resulting suspension was filtered and the filter cake washed with water (2 mL). The filter cake was dried to constant weight under vacuum at 40° C. to afford a 100% yield (292 mg) of 9 as a white solid: mp 124-125° C.; 1H NMR (500 MHz, CDCl3) δ 7.93 (s, 1H), 3.10 (s, 2H), 1.34 (5, 6H); MS (ESI+) m/z 211.0 (M+H).

Workup

  1. customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. customAfter this time, the organic solvents were removed under reduced pressure, water (6 mL)
  4. additionwas added
  5. filtrationThe resulting suspension was filtered
  6. washthe filter cake washed with water (2 mL)
  7. customThe filter cake was dried to constant weight under vacuum at 40° C.

Sources & evidence

ORD record
ord-12a8a035669e4f2cbd5c758c4c700b90
Source dataset
uspto-grants-2013_12
Patent number
US08598174B2

Reaction notes

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