Ethanol → HCID 59331598, compound

HRID 1882046Notes

Reaction equation

HRID 1882046 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:13](=O)[CH:14]=[CH2:15])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(O)C.O1CCCC1.[OH:32][CH:33]([C:38]1[CH:39]=[CH:40][C:41]([CH:44]=O)=[N:42][CH:43]=1)[C:34]([OH:37])([CH3:36])[CH3:35].C([N:48](CC)CC)C>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([C:13]2[NH:48][C:44]([C:41]3[N:42]=[CH:43][C:38]([CH:33]([OH:32])[C:34]([CH3:36])([OH:37])[CH3:35])=[CH:39][CH:40]=3)=[CH:15][CH:14]=2)[CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

7

Reactant 5

HCID 702EthanolHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 593312984-[3-chloro-4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-oneHCID 593314885-(1,2-Dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde

Product 1

HCID 59331598HCID 59331598, compoundYield 87%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
70 °C

Procedure

A solution of 4-[3-chloro-4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (0.600 g) in a mixed 10 solvent of ethanol (5 mL) and tetrahydrofuran (5 mL) was deaerated, and 5-(1,2-dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde (491 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (45 mg) and triethylamine (0.093 mL) were added. The reaction solution was purged with nitrogen, and stirred at 70° C. for 1 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 (15 mL) was added ammonium acetate (647 mg), 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=30:70-100:0, volume ratio) and recrystallized from hexane-ethyl acetate to give the title compound (0.777 g, yield 87%) as colorless crystals. MS: 533 (MH+). melting point 138-140° C.

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 (15 mL) was added ammonium acetate (647 mg)
  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=30:70-100:0, volume ratio)
  14. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-f537ccaf0fb9492a8d8a2bbf8a75beff
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…