Water → HCID 58168549, compound

HRID 1255269Notes

Reaction equation

HRID 1255269 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH2:16][C:17]#N)[S:14][CH:15]=1)(C(C)(C)C)(C)C.[OH-:19].[K+].[OH2:21]>C(O)C>[OH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH2:16][C:17]([OH:21])=[O:19])[S:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 58168477HCID 58168477, compound2×

Product 1

HCID 58168549HCID 58168549, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-(4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)acetonitrile [Aromatic Intermediate 20, step b] (4.20 g) dissolved in ethanol (30 mL) was added to a stirred solution of potassium hydroxide (1.67 g) in water (30 mL). The resulting mixture was stirred at 100° C. for 3 hours. The mixture was partitioned between aqueous brine and ethyl acetate, and the phases separated. The aqueous layer was cooled with ice and acidified by dropwise addition of concentrated hydrochloric acid. The aqueous layer was then extracted with ethyl acetate (×2), the combined organic phases were washed with aqueous brine, dried over sodium sulphate and the solvent evaporated under reduced pressure to give a yellow solid which was triturated with ether (20 mL) to give the subtitled compound. Yield 2.33 g.

Workup

  1. customThe mixture was partitioned between aqueous brine and ethyl acetate
  2. customthe phases separated
  3. temperatureThe aqueous layer was cooled with ice
  4. additionacidified by dropwise addition of concentrated hydrochloric acid
  5. extractionThe aqueous layer was then extracted with ethyl acetate (×2)
  6. washthe combined organic phases were washed with aqueous brine
  7. dry with materialdried over sodium sulphate
  8. customthe solvent evaporated under reduced pressure
  9. customto give a yellow solid which
  10. customwas triturated with ether (20 mL)

Sources & evidence

ORD record
ord-2788fe5ff4244dd29014d8304a7f6986
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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