Acetic Acid → HCID 178445822, compound

HRID 1727331Notes

Reaction equation

HRID 1727331 reaction equation
[OH-].[Na+].[CH:3]([CH:6]([C@H:16]1[CH2:19][C@H:18](C2C=C([N+]([O-])=O)C=CC=2C([O-])=O)[CH2:17]1)[C:7]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[O:8][SiH3:9])([CH3:5])[CH3:4].CC(O)=[O:34]>O1CCOCC1>[CH:3]([CH:6]([C@H:16]1[CH2:17][C@H:18]([OH:34])[CH2:19]1)[C:7]([CH:10]([CH3:11])[CH3:12])([CH:13]([CH3:15])[CH3:14])[O:8][SiH3:9])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 178445817HCID 178445817, compound

Product 1

HCID 178445822HCID 178445822, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Aqueous NaOH (0.4 mol/L, 12 mL, 4.56 mmol) was added to a stirred solution of trans-3-(triisopropyl-siloxyethyl)cyclobutyl-4-nitrobenzoate (0.96 g, 2.28 mmol) in 18 mL 1,4-dioxane at ambient temperature. After 1 hr, AcOH was added drop by drop. After 5 min, the reaction mixture was concentrated by rotovap. The residue was partitioned between EtOAc (10 mL) and saturated NaHCO3 (2×10 mL). The organic phase was dried over MgSO4 and solvent evaporation gave light yellow oil (0.57 g, 92.3%, Rf=0.23 (Hexane:EtOAc=9:1)). 1H NMR (CDCl3, 300 MHz): δ 1.00-1.07 (m, 21H), 1.63-1.70 (m, 2H), 1.78 (bs, 1H), 1.99-2.10 (m, 4H), 2.24-2.38 (m, 1H), 3.61-3.65 (t, J=6.6, 2H), 4.35-4.44 (m, 1H). 13C NMR (CDCl3, 75 MHz): δ 12.23, 18.29, 24.24, 38.05, 39.37, 62.27, 66.82. MS (FAB): expected for C15H32O2Si (M+H)+ 273.50. Found 273.22456.

Workup

  1. waitAfter 5 min
  2. concentrationthe reaction mixture was concentrated by rotovap
  3. customThe residue was partitioned between EtOAc (10 mL) and saturated NaHCO3 (2×10 mL)
  4. dry with materialThe organic phase was dried over MgSO4 and solvent evaporation
  5. customgave light yellow oil (0.57 g, 92.3%, Rf=0.23 (Hexane:EtOAc=9:1))

Sources & evidence

ORD record
ord-abef13675f354104ad461796de73c9be
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

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