Acetic Acid → HCID 178521630, compound

HRID 1641509Notes

Reaction equation

HRID 1641509 reaction equation
[OH-].[Na+].[N+](C1C=CC(C([O:12][C@H:13]2[CH2:16][C@H:15]([CH2:17][CH2:18][O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:14]2)=O)=CC=1)([O-])=O.CC(O)=O>O1CCOCC1>[CH2:20]([O:19][CH2:18][CH2:17][C@H:15]1[CH2:14][C@H:13]([OH:12])[CH2:16]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 178525792HCID 178525792, compound

Product 1

HCID 178521630HCID 178521630, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Aqueous NaOH (0.4 mol/L, 52 mL, 20.8 mmol) was added to a stirred solution of trans-3-(benzyloxyethyl)cyclobutyl 4-nitrobenzoate (3.7 g, 10.4 mmol) in 80 mL 1,4-dioxane at ambient temperature. After 40 min, AcOH (0.9 mL, 15.4 mmol) was added drop by drop. After 5 min, the reaction mixture was concentrated by rotovap. The residue was partitioned between EtOAc (50 mL) and saturated NaHCO3 (2×50 mL). The organic phase was dried over MgSO4 and solvent evaporation gave light yellow oil (2.09 g, 97.5%). 1H NMR (CDCl3, 300 MHz): δ 1.71-1.78 (m, 2H), 1.94 (bs, 1H), 2.03-2.07 (m, 3H), 2.60-2.74 (m, 1H), 3.40-3.45 (t, J=6.9, 2H), 4.49 (s, 2H), 7.27-7.37 (m, 5H). 13C NMR (CDCl3, 75 MHz): δ 24.58, 36.11, 37.90, 39.95, 66.63, 69.17, 73.10, 127.65, 127.69, 128.45, 138.60.

Workup

  1. waitAfter 5 min
  2. concentrationthe reaction mixture was concentrated by rotovap
  3. customThe residue was partitioned between EtOAc (50 mL) and saturated NaHCO3 (2×50 mL)
  4. dry with materialThe organic phase was dried over MgSO4 and solvent evaporation

Sources & evidence

ORD record
ord-9cc95edd5f6942309efb6255f0dfd20f
Source dataset
uspto-grants-2012_02
Patent number
US08114994B2

Reaction notes

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