Ethyl Acetate → HCID 69627832, compound

HRID 324060Notes

Reaction equation

HRID 324060 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]([OH:16])=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:30][C:31]([O:33][CH3:34])=[O:32].CCOC(C)=O>CN(C=O)C.O>[CH3:34][O:33][C:31](=[O:32])[CH2:30][O:16][C:7]1[C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 6259854-Nitro-2,6-diphenylphenol

Product 1

HCID 69627832HCID 69627832, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5′-nitro-[1,1′;3′1″]terphenyl-2′-ol (0.250 g, 0.858=mmol) and K2CO3 (0.130 g, 0.944 mmol) in DMF (9 mL) at room temperature was added dropwise methyl bromoacetate (0.162 mL, 1.72 mmol). After 72 h at this temperature, it was diluted with H2O (20 mL) followed by excess EtOAc (200 mL). The organic layer was washed with 1 N HCl (50 mL), sat. aq. NaHCO3 (50 mL), and brine (50 mL) and then dried (MgSO4). After concentration, the residue was purified by flash chromatography (5 to 30% acetone/hexane gradient) to afford the product (0.309 g, 99%) as a clear oil; 1H NMR (DMSO-d6) δ3.37 (s, 3H), 4.03 (s, 2H), 7.43-7.53 (m, 6H), 7.60-7.64 (m, 4H), 8.14 (s, 2H); IR (film) 3420, 3080, 2950, 1770, 1745, 1590, 1530, 1500, 1455, 1440, 1410, 1350, 1305, 1210, 1110, 1070, 910, 745, and 700 cm−1; mass spectrum [EI], m/z 363 (M)+; Anal. Calcd. for C21H17NO5.0.75H2O: C, 66.93; H, 4.95; N, 3.72, Found: C, 66.89; H, 4.67; N, 3.51.

Workup

  1. washThe organic layer was washed with 1 N HCl (50 mL), sat. aq. NaHCO3 (50 mL), and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationAfter concentration
  4. customthe residue was purified by flash chromatography (5 to 30% acetone/hexane gradient)

Sources & evidence

ORD record
ord-7205d94d601a4e54b91de976d9e3bc85
Source dataset
uspto-grants-2001_04
Patent number
US06214877B1

Reaction notes

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