Tetrahydrofuran → HCID 85719857, compound

HRID 902907Notes

Reaction equation

HRID 902907 reaction equation
[C:1]([O:5][C:6](=[O:13])[CH2:7][C:8](=[CH2:12])[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].[S:14]1C=CC=C1CC(O)=O.C1C[O:26][CH2:25][CH2:24]1>>[C:1]([O:5][C:6](=[O:13])[CH2:7][CH:8]([CH2:12][S:14][C:25](=[O:26])[CH3:24])[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 159702-Thiopheneacetic acidHCID 18314732HCID 18314732, compound

Product 1

HCID 85719857HCID 85719857, compoundYield 42.6%

Procedure

To a stirring solution of the compound of example 23 (3.00 g, 16.11 mmoles) in anhydrous THF (16 mL), was added drop wise thiolacetic acid (3.68 g, 48.34 mmoles). The mixture was stirred at room temperature for 24 hours. The solvent was then evaporated under vacuum and the residue was directly purified by flash chromatography (SiO2, 20% ethyl acetate:80% hexanes) to afford 1.80 g (42.6% yield) of the desired product as a yellow oil. IR (film) 2980, 2652, 1729, 1255, 1152 cm−1; HRMS (EI) Calcd for C11H19O5S: 263.0953, Found: 263.0944.

Workup

  1. customThe solvent was then evaporated under vacuum
  2. customthe residue was directly purified by flash chromatography (SiO2, 20% ethyl acetate:80% hexanes)

Sources & evidence

ORD record
ord-534dfcc669524866b1bd0dc883370a54
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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