Sulfuric Acid → HCID 58134741, compound

Reaction equation

OS(O)(=O)=O.O[C:7]1([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][CH2:9][CH2:8]1.[C:17](#[N:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-:25].[Na+]>>[C:17]([NH:24][C:7]1([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][CH2:9][CH2:8]1)(=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Reactant 4

HCID 1118Sulfuric Acid

HCID 7505Benzonitrile

HCID 14798Sodium Hydroxide

HCID 58134840ETHYL 2-(1-HYDROXYCYCLOBUTYL)ACETATE

Product 1

HCID 58134741HCID 58134741, compoundYield 51%

Procedure

H2SO4 (2.20 mL, 41.3 mmol) was slowly added to a mixture of ethyl 1-hydroxycyclobutylacetate (6.45 g, 40.8 mmol) and benzonitrile (40 mL, 0.392 mol) at room temperature. The mixture was stirred for 1 hour at room temperature, then for an additional hour at 80° C. The mixture was cooled in an ice-water bath, and 2N NaOH solution was added until the mixture reached pH=7. The mixture was extracted with ethyl acetate and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. Flash chromatography (AcOEt:Hexane=5:1) of the residue gave the title compound as a colorless solid (5.40 g, 51%). 1H-NMR (400 MHz, CDCl3) δ 1.22 (3H, t, J=7.3 Hz), 1.84-2.07 (2H, m), 2.22-2.32 (2H, m), 2.44-2.55 (2H, m), 3.05 (2H, s), 4.11 (2H, q, J=7.3 Hz), 6.73 (1H, s), 7.39-7.52 (3H, m), 7.72-7.79 (2H, m).