Ethyl Acetate → HCID 69627832, compound

HRID 1743426Notes

Reaction equation

HRID 1743426 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) δ 3.37 (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-4da8bea279d748febfd1ccbb2fbd81a5
Source dataset
uspto-grants-2006_03
Patent number
US07008636B2

Reaction notes

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