Ethanol → HCID 59331403, compound

HRID 1882047Notes

Reaction equation

HRID 1882047 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:12](=O)[CH:13]=[CH2:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(O)C.O1CCCC1.[OH:31][CH:32]([C:37]1[CH:38]=[CH:39][C:40]([CH:43]=O)=[N:41][CH:42]=1)[C:33]([OH:36])([CH3:35])[CH3:34].C([N:47](CC)CC)C>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1>[CH3:34][C:33]([OH:36])([CH3:35])[CH:32]([C:37]1[CH:42]=[N:41][C:40]([C:43]2[NH:47][C:12]([CH:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[CH2:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:13][CH:14]=2)=[CH:39][CH:38]=1)[OH:31]

Participants

7

Reactant 5

HCID 702EthanolHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 593314885-(1,2-Dihydroxy-2-methylpropyl)pyridine-2-carbaldehydeHCID 684337694-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

Product 1

HCID 59331403HCID 59331403, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalyst

Conditions

Temperature
70 °C

Procedure

A solution of 4-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (1.79 g) in a mixed solvent of ethanol (30 mL) and tetrahydrofuran (30 mL) was deaerated, and 5-(1,2-dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde (1.52 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (150 mg) and triethylamine (0.310 mL) were added. The reaction solution was purged with nitrogen, and the mixture was stirred at 70° C. for 1.5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To a solution of the residue in acetic acid (150 mL) was added ammonium acetate (4.28 g), and the mixture was stirred at 110° C. for 2 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-100:0, volume ratio) to give the title compound (1.79 g, yield 65%) as a colorless amorphous solid. MS: 499 (MH+).

Workup

  1. customThe reaction solution was purged with nitrogen
  2. additionWater was added to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo a solution of the residue in acetic acid (150 mL) was added ammonium acetate (4.28 g)
  8. stirringthe mixture was stirred at 110° C. for 2 hr
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed successively with water and saturated brine
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=20:80-100:0, volume ratio)

Sources & evidence

ORD record
ord-0e8cb61e49cf4ad8941d076209031828
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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