Ethanol → HCID 86699863, compound

HRID 1772117Notes

Reaction equation

HRID 1772117 reaction equation
[Br:1][C:2]1[C:3]([CH2:23][O:24][Si](C(C)(C)C)(C)C)=[C:4]([NH:8][CH2:9][C:10]2[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[S:12][C:11]=2[C:19]([O:21]C)=[O:20])[CH:5]=[CH:6][CH:7]=1.[OH-].[Li+].C1COCC1.C(O)C>O>[Br:1][C:2]1[C:3]([CH2:23][OH:24])=[C:4]([NH:8][CH2:9][C:10]2[CH:14]=[C:13]([C:15]([CH3:16])([CH3:17])[CH3:18])[S:12][C:11]=2[C:19]([OH:21])=[O:20])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86699864HCID 86699864, compound

Product 1

HCID 86699863HCID 86699863, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50-mL single-necked round-bottomed flask equipped with a magnetic stirrer was charged with 114e (1.10 g, 2.09 mmol), lithium hydroxide (201 mg, 8.36 mmol), THF (10 mL), ethanol (10 mL) and water (10 mL). After stirring at room temperature for 2 h, the solvent was removed under reduced pressure and the resulting residue was acidified with 2N hydrochloric acid to pH of 4. The resulting aqueous solution was extracted with ethyl acetate (3×30 mL), and the organic extracts were combined and dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography to afford 114f in 65% yield (540 mg) as a white solid: mp 68-69° C.; 1H NMR (500 MHz, CDCl3) δ 7.03-6.97 (m, 2H), 6.86 (s, 1H), 6.71 (d, 1H, J=8.0 Hz), 4.94 (s, 2H), 4.60 (s, 2H), 1.35 (s, 9H); MS (ESI+) m/z 398.0 (M+H).

Workup

  1. customA 50-mL single-necked round-bottomed flask equipped with a magnetic stirrer
  2. customthe solvent was removed under reduced pressure
  3. extractionThe resulting aqueous solution was extracted with ethyl acetate (3×30 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8e1045b8978946c9afdc5681d000a475
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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