Ethanol → HCID 13606748, compound

HRID 1380103Notes

Reaction equation

HRID 1380103 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[CH:13]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:17]([CH3:24])[NH:16][C:15]([CH3:25])=[C:14]1[C:26]([O:28][CH2:29][CH3:30])=[O:27].B(Br)(Br)Br.C([O-])([O-])=O.[K+].[K+].C(O)C>ClCCCl>[CH3:24][C:17]1[NH:16][C:15]2([CH3:25])[CH:14]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:13]([C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:4]1[C:5]3[C:10]([CH:11]=[CH:12][C:3]=1[O:2]2)=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 13606747HCID 13606747, compound

Product 1

HCID 13606748HCID 13606748, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2.25 g (5.5 mm) of diethyl 1,4-dihydro-4-(2-methoxy-1-naphthalenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate 20 in 12.0 mL of dry 1,2-dichloroethane was stirred under Ar at 25° C. and treated with 2.40 g (7.68 mm) of BBr3.CH3SCH3 complex. After stirring at 25° C. for 20 hours, 10.0 g of anhydrous powdered K2CO3 and 100 mL of absolute ethanol were added. Stirring was continued for 60 hours at 25°. The reaction was quenched with saturated aqueous NH4Cl and extracted with 500 ml of CH2Cl2. The organic layer was washed with pH 7 phosphate buffer and brine, dried (anhydrous Na2SO4), filtered, evaporated and flash chromatographed (silica gel, 2% acetone in CH2Cl2).

Workup

  1. stirringStirring
  2. waitwas continued for 60 hours at 25°
  3. customThe reaction was quenched with saturated aqueous NH4Cl
  4. extractionextracted with 500 ml of CH2Cl2
  5. washThe organic layer was washed with pH 7 phosphate buffer and brine
  6. dry with materialdried (anhydrous Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customflash chromatographed (silica gel, 2% acetone in CH2Cl2)

Sources & evidence

ORD record
ord-bd694a4f6ffc4d48af07a54c55e1e0f4
Source dataset
uspto-grants-1986_04
Patent number
US04579851

Reaction notes

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