1,3-Propanediol → HCID 2987227, compound

HRID 853870Notes

Reaction equation

HRID 853870 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[O:12].[CH2:13](O)[CH2:14][CH2:15][OH:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]12[O:16][CH2:15][CH2:14][CH2:13][O:12]1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 118405-MethylisatinHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 2987227HCID 2987227, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5-methylisatin (8.00 g, 49.6 mmol), 1,3 propanediol (10.89 mL, 149 mmol, 3 eq) and p-toluenesulfonic acid monohydrate (1.89 g, 9.92 mmol, 0.2 eq) in benzene (940 mL) was heated to reflux under a Dean Stark Trap for 17.5 hr. The reaction mixture was concentrated. The residue was taken up in EtOAc (300 mL) and washed with sat. aq. NaHCO3 (2×) and concentrated. The crude product was purified on Biotage KP silica gel eluting with 60/40 Pet ether/EtOAc to give the title compound as a yellow solid (8.0 g., 74% yield). NMR (300 Mz, DMSO-d6): consistent.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under a Dean Stark Trap for 17.5 hr
  3. concentrationThe reaction mixture was concentrated
  4. washwashed with sat. aq. NaHCO3 (2×)
  5. concentrationconcentrated
  6. customThe crude product was purified on Biotage KP silica gel eluting with 60/40 Pet ether/EtOAc

Sources & evidence

ORD record
ord-a78d55d0f97d4762b2f2d76363b86530
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

Loading…