Methanol → HCID 66748410, compound

HRID 2402105Notes

Reaction equation

HRID 2402105 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[S:14][C:13]=1[C:23]([O:25]CC)=[O:24].CO.O1CCCC1.O.[OH-].[Li+]>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[CH:16]=[C:15]([C:17]2[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=2)[S:14][C:13]=1[C:23]([OH:25])=[O:24]

Participants

6

Reactant 5

HCID 887MethanolHCID 962Water2×HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66748007HCID 66748007, compound

Product 1

HCID 66748410HCID 66748410, compound

Procedure

Ethyl 3-(2-naphthylmethyl)-5-pyridin-4-ylthiophene-2-carboxylate (80.0 mg, 0.214 mmol) was placed in a round bottomed flask equipped with a stirbar. Methanol (3 mL, 70 mmol) and tetrahydrofuran (3 mL, 40 mmol) were added followed by water (2 mL, 100 mmol). The resulting solution was stirred and lithium hydroxide in water (1.0 M, 0.643 mL, 0.643 mmol) was added. The flask was sealed and stirred overnight at RT. LCMS of an aliquot indicated that all starting material had been consumed to give a single product with the correct mass for the desired product. To the stirring reaction was added ˜30 mL water and a few mL saline. The mixture was stirred and acidified to ˜pH 1 with 1N HCl—a gelatinous precipitate formed. The mixture was stirred rapidly and diethyl ether (10 mL) was added—the precipitate became more granular and became suspended mostly in the organic layer. The quench mixture was stirred at room temperature for ˜30 minutes then the solid was collected on a fritted funnel, washed well with water then diethyl ether, then dried in vacuo to yield product 60 mg (81% yield) as a white powder. LC/MS (FA) ES+ 346. 1H NMR (400 MHz, DMSO) δ 13.62-13.20 (s, 1H), 8.63-8.52 (dd, J=4.7, 1.5 Hz, 2H), 7.91-7.80 (m, 3H), 7.80-7.72 (d, J=3.0 Hz, 2H), 7.70-7.63 (dd, J=4.6, 1.5 Hz, 2H), 7.53-7.40 (m, 3H), 4.57-4.48 (s, 2H).

Workup

  1. customequipped with a stirbar
  2. customThe flask was sealed
  3. stirringstirred overnight at RT
  4. customhad been consumed

Sources & evidence

ORD record
ord-3299c0914f1f456e92e8948a9b609571
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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