Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 86690117, compound

HRID 520407Notes

Reaction equation

HRID 520407 reaction equation
[O:1]=[C:2]1[CH2:14][CH2:13][C:5]2([C@@H:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6]2)[CH2:4][CH2:3]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CC(C)=O.O.CCOC(C)=O>[O:1]=[C:2]1[CH2:14][CH2:13][C:5]2([CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6]2)[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86690116HCID 86690116, compound

Product 1

HCID 86690117HCID 86690117, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl (1S)-6-oxospiro[2.5]octane-1-carboxylate (1.9 g, 7.91 mmol) in acetone (20 mL) and water (5 mL) was added PPTS (0.1 g, 0.398 mmol). The reaction mixture was heated at 60° C. for 5 h, and then stirred at rt for 45 h. The reaction mixture was diluted with EtOAc, washed with water, brine, dried (MgSO4) and concentrated to afford ethyl 6-oxospiro[2.5]octane-1-carboxylate as an oil (1.32 g). 1H NMR (400 MHz, CDCl3) δ ppm 4.13-4.21 (2H, m), 2.35-2.51 (3H, m), 2.19-2.30 (1H, m), 2.00-2.09 (3H, m), 1.86 (1H, ddd, J=13.68, 8.16, 5.27 Hz), 1.64-1.77 (2H, m), 1.23-1.35 (3H, m), 1.08 (1H, dd, J=8.16, 4.64 Hz).

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3b40d98295d5475ea63a34a119964709
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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