Methanol → HCID 66747476, compound

HRID 2402103Notes

Reaction equation

HRID 2402103 reaction equation
[OH:1][CH:2]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1)[C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][C:4]=1[C:14]([O:16]CC)=[O:15].O1CCCC1.CO.[OH-].[Na+]>O>[OH:1][CH:2]([C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=1)[C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[S:5][C:4]=1[C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66748221HCID 66748221, compound

Product 1

HCID 66747476HCID 66747476, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 3-[hydroxy(2-naphthyl)methyl]-5-pyridin-4-ylthiophene-2-carboxylate (70.0 mg, 0.180 mmol) was placed in a round bottomed flask equipped with a stirbar. Tetrahydrofuran (2.00 mL), methanol (1.00 mL), and water (1.50 mL) were added with stirring—all solids dissolved. Sodium hydroxide (1.0 M, 1.50 mL, 1.50 mmol) was added in a single portion and the resulting solution was stirred under an atmosphere of nitrogen overnight, resulting in a clear light yellow solution. The reaction was quenched into water and the pH of the mixture was adjusted the pH to ˜6-6.5 with sodium bicarbonate solution. The mixture was extracted with ethyl acetate, the extracts were combined and then rotovapped to leave crude product as a light yellow solid. The crude product was purified by HPLC to yield 9 mg (14% yield) product as a pale yellow powder. LC/MS (FA) ES+ 362. 1H NMR (400 MHz, DMSO) δ 8.60-8.51 (d, J=6.1 Hz, 2H), 7.98-7.94 (s, 2H), 7.91-7.75 (m, 4H), 7.68-7.58 (m, 3H), 7.53-7.37 (m, 2H), 6.64-6.36 (s, 1H).

Workup

  1. customequipped with a stirbar
  2. dissolutiondissolved
  3. stirringthe resulting solution was stirred under an atmosphere of nitrogen overnight
  4. customresulting in a clear light yellow solution
  5. customThe reaction was quenched into water
  6. extractionThe mixture was extracted with ethyl acetate
  7. customto leave crude product as a light yellow solid
  8. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-f3485c7df001475da8452bc90a62e303
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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