Hydrochloric Acid → HCID 54257517, compound

HRID 343562Notes

Reaction equation

HRID 343562 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([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)[S:8][CH:9]=1)([O:3]C)=[O:2].[OH-].[K+].O.Cl>O1CCCC1.CO>[C:1]([C:5]1[CH:6]=[C:7]([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)[S:8][CH:9]=1)([OH:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 54202301HCID 54202301, compound

Product 1

HCID 54257517HCID 54257517, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4-carbomethoxythien-2-ylethynyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.12 g, 0.427 mmol) and coarsely ground potassium hydroxide (0.045 g, 0.81 mmol) in tetrahydrofuran (2.5 mL), methanol (2.5 mL), and water (0.5 mL) was stirre at room temperature under an argon atmosphere for three days. 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 0.25:2.5:97.5 acetic acid:methanol:dichloromethane, provided 4-(4-carboxythien-2-ylethynyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one as an off- white foam (0.11 g, 94%), mp 75°-76° C. Anal. (C25H26O5S.0.25 H2O) calcd: C, 67.78; H, 6.03; found: C, 67.73; H, 5.80.

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 0.25:2.5:97.5 acetic acid

Sources & evidence

ORD record
ord-cd34720400d34bdaad20ff982379989f
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

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