Hydrochloric Acid → 3-[4-(2-Methyl-benzylsulfanyl)-phenyl]-hex-4-ynoic acid

HRID 1160294Notes

Reaction equation

HRID 1160294 reaction equation
CC1(C)OC(=O)[CH:5]([CH:9]([C:13]2[CH:18]=[CH:17][C:16]([S:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH3:27])=[CH:15][CH:14]=2)[C:10]#[C:11][CH3:12])[C:4](=[O:28])[O:3]1.N1C=CC=CC=1.Cl>O>[CH3:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][S:19][C:16]1[CH:17]=[CH:18][C:13]([CH:9]([C:10]#[C:11][CH3:12])[CH2:5][C:4]([OH:28])=[O:3])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 591326202,2-Dimethyl-5-{1-[4-(2-methyl-benzylsulfanyl)-phenyl]-but-2-ynyl}-[1,3]dioxane-4,6-dione

Product 1

HCID 591326523-[4-(2-Methyl-benzylsulfanyl)-phenyl]-hex-4-ynoic acidYield 111%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 28.3 (20 mg, 0.05 mmol) in 5:1 pyridine:water (6 mL) was heated to 80° C. for 72 hours. The reaction was poured into 500 mL of water and the solution was acidified with 1N HCl(aq) (65 mL). The aqueous solution was extracted with ethyl acetate and the combined organic layers were washed with water, followed by brine. The combined organic layers were then dried (Na2SO4) and concentrated in vacuo. The resultant residue was then purified via radial chromatography (30% ethyl acetate in hexanes) to yield 18 mg (quantitative) 3-[4-(2-Methyl-benzylsulfanyl)-phenyl]-hex-4-ynoic acid (28). LC/MSD m/e: 323.1 (M−H).

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate
  2. washthe combined organic layers were washed with water
  3. dry with materialThe combined organic layers were then dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was then purified via radial chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-04492a15ae904bb68f5765e4ad42f4c2
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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