1,1-Dichloroethane → HCID 87106246, compound

HRID 922178Notes

Reaction equation

HRID 922178 reaction equation
ClC(Cl)C.[CH3:5][O:6][N:7]=[C:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.[CH3:25][O:26][C:27](=[O:37])[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[CH:32][CH:31]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:5][O:6]/[N:7]=[C:8](/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)\[CH2:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:36][C:33]2[CH:32]=[CH:31][C:30]([CH2:29][CH2:28][C:27]([O:26][CH3:25])=[O:37])=[CH:35][CH:34]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 63651,1-DichloroethaneHCID 417374Methyl 3-(4-aminophenyl)propanoateHCID 5049666Sodium triacetoxyborohydrideHCID 123600731HCID 123600731, compound

Product 1

HCID 87106246HCID 87106246, compoundYield 69.4%

Conditions

Temperature
0 °C

Procedure

To a 50 mL RB flask fitted with magnetic stirrer was charged 5 mL of dichloroethane. To the stirred solvent was added 4-(2-methoxyimino-2-phenyl-ethoxy)-benzaldehyde (0.4 g, 1.5 mmol), 3-(4-amino-phenyl)-propanoic acid methyl ester (0.27 g, 1.5 mmol). RM was cooled to 0° C. and sodium triacetoxyborohydride (0.47 g, 2.25 mmol) was added portion wise over a period of 15 minutes. The reaction mixture was stirred at RT for 2 h. The RM was quenched with NaHCO3 solution (40 mL 10% solution in water) and extracted with ethyl acetate (20 mL×2). The organic layer washed with saturated brine solution (25 mL), dried over anhydrous Na2SO4 and evaporated in vacuum to dryness. The resulting crude compound was purified by column chromatography on silica gel (100/200 mesh), using petroleum ether (60-80) and ethyl acetate as eluent to give the product (0.450 g, Yield: 69.4%): MS (ESI, 120 eV): m/z=433.1 (M+H)+.

Workup

  1. customTo a 50 mL RB flask fitted with magnetic stirrer
  2. customThe RM was quenched with NaHCO3 solution (40 mL 10% solution in water)
  3. extractionextracted with ethyl acetate (20 mL×2)
  4. washThe organic layer washed with saturated brine solution (25 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated in vacuum to dryness
  7. customThe resulting crude compound was purified by column chromatography on silica gel (100/200 mesh)

Sources & evidence

ORD record
ord-a1846dcdd6184e7dabb3da438a63ffaa
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

Loading…