2,4-Pentanediol → N-Acetyl-2-pyrroline

HRID 978182Notes

Reaction equation

HRID 978182 reaction equation
[C:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[O:9]C)(=[O:3])[CH3:2].CC(O)CC(O)C.CN1CCCC1=O>O.CCOC(C)=O>[C:1]([N:4]1[CH2:8][CH2:7][CH:6]=[CH:5]1)(=[O:3])[CH3:2].[C:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[OH:9])(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 122622,4-Pentanediol2×HCID 13387N-methyl-2-pyrrolidoneHCID 127112051-(2-Methoxypyrrolidin-1-yl)ethan-1-one2×

Product 2

HCID 10909522N-Acetyl-2-pyrrolineHCID 13113443N-acetyl-2-hydroxypyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Reaction of N-Acetyl-2-methoxypyrrolidine (E) with 2,4-Pentandiol. One g of N-acetyl-2-methoxypyrrolidine (largely E plus lesser an amounts of B, C and D), 0.9 g of 2,4-pentandiol and 240 mg of N-methyl-2-pyrrolidone internal standard were heated at 50°-55° C. in 1 mL of H2O. A separate sample was heated in 1 mL of EtOAc. Results in both samples were similar: rapid initial formation of a small peak at 8.02 min (cyclic hemiamidal of the diol?), followed by growth of major product peaks at 8.35 and 8.73 min, the epimeric cyclic acetals. Small quantities of dehydrated product G (r.t.=4.75 min), and, in the aqueous sample, N-acetyl-2-hydroxypyrrolidine, F (before A at ~5.6 min) were also produced. One of the diols appeared to react faster and to a greater extent than the other. Measurements at 3-4 hr were close to the overnight values: ~87% conversion of A, 60-70% of B and essentially quantitative conversion of C and D.

Workup

  1. customResults in both samples
  2. customfollowed by growth of major product peaks at 8.35 and 8.73 min

Sources & evidence

ORD record
ord-b5f5beaa7d5b4d87b8fa96650d8bee71
Source dataset
uspto-grants-1987_05
Patent number
US04663410

Reaction notes

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