Hydrochloric Acid → HCID 54262504, compound

HRID 343561Notes

Reaction equation

HRID 343561 reaction equation
[C:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]#[C:11][C:12]2([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)[CH:20]=3)[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]2)[CH:9]=1)([O:3]C)=[O:2].[OH-].[K+].O.Cl>O1CCCC1.CO>[C:1]([C:5]1[S:6][CH:7]=[C:8]([C:10]#[C:11][C:12]2([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH:28]4[CH2:29][CH2:30][CH2:31][CH2:32]4)[CH:20]=3)[CH2:13][CH2:14][C:15](=[O:18])[CH2:16][CH2:17]2)[CH:9]=1)([OH:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 54536269HCID 54536269, compound

Product 1

HCID 54262504HCID 54262504, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(2-carbomethoxythien-4-ylethynyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.19 g, 0.43 mmol) and coarsely ground potassium hydroxide (0.036 g, 0.64 mmol) in tetrahydrofuran (2 mL), methanol (2 mL), and water (0.4 mL) was stirred at room temperature under an argon atmosphere for 24 h. The reaction was acidified (10% HCl), was extracted three times with 5:95 methanol:dichloromethane, was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 0.1:3:97 acetic acid:methanol:dichloromethane, provided 4-(2-carboxythien-4-ylethynyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one as an off-white solid (0.18 g, 95%), mp 80°-82° C. Anal. (C25H26O5S.0.25 H2O) calcd: C, 67.78; H, 6.03; found: C, 67.72; H, 6.02.

Workup

  1. extractionwas extracted three times with 5:95 methanol
  2. dry with materialdichloromethane, was dried (magnesium sulfate)
  3. customwas evaporated
  4. customPurification by flash chromatography
  5. washeluting with 0.1:3:97 acetic acid

Sources & evidence

ORD record
ord-c382bc84154048aeb4bfb1adf2b1209f
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

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