Acetic Anhydride → HCID 11164425, compound

HRID 431746Notes

Reaction equation

HRID 431746 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](CCO)=[C:18]([N+:29]([O-:31])=[O:30])[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:5]([O:4][CH2:1][CH2:2][C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:17][C:18]=1[N+:29]([O-:31])=[O:30])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11393125HCID 11393125, compound

Product 1

HCID 11164425HCID 11164425, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (0.35 mL, 3.71 mmol) was added to a solution of 2-[4-benzyloxy-2-nitronaphthalen-1-yl]ethanol ((0.3 g, 0.93 mmol) in dry pyridine (3 mL) at room temperature and stirred overnight. The mixture was concentrated and dissolved in AcOEt (50 mL). The organic layer was washed with 1 M HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and saturated aqueous NaCl (10 mL), and then the organic layer was dried (Na2SO4) and concentrate. The residue was purified by silica-gel column (AcOEt: Petroleum ether=1: 6) to yield 2-[4-benzyloxy-2-nitronaphthalen-1-yl]ethyl acetate ((0.21 g, 62%) as a yellow solid. mp 82-87° C.; 1H NMR (CDCl3, 500 MHz) δ 8.43 (d, 8.5, 1H), 8.33 (d, 8.5, 1H), 7.33 (dt, 1.0, 7.5, 1H), 7.66 (dt, 1.0, 7.0, 1H), 7.54 (d, 7.5, 2H), 7.45 (t, 7.5, 2H), 7.40 (t, 7.0, 1H), 7.28 (s, 1H), 5.30 (s, 2H), 4.47 (t, 7.0, 2H), 3.55 (t, 7.0, 2H), 2.06 (s, 3H); EIMS m/z 388 (M+Na+); IR (neat) νmax 1738, 1593, 1527, 1514, 1466, 1424, 1365, 1337, 1235, 1104, 1043, 770, 752, 698 cm−1.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutiondissolved in AcOEt (50 mL)
  3. washThe organic layer was washed with 1 M HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and saturated aqueous NaCl (10 mL)
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. concentrationconcentrate
  6. customThe residue was purified by silica-gel column (AcOEt: Petroleum ether=1: 6)

Sources & evidence

ORD record
ord-b2a4bd3b36af4ecfb6bf9da4c3f3ab5c
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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