1-Butanol, 4-methoxy- → HCID 22253034, compound

HRID 1612470Notes

Reaction equation

HRID 1612470 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:37][O:38][CH2:39][CH2:40][CH2:41][CH2:42]O.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:37][O:38][CH2:39][CH2:40][CH2:41][CH2:42][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 81071-Butanol, 4-methoxy-HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22252977Methyl 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoate

Product 1

HCID 22253034HCID 22253034, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-hydroxy-5-(2-oxopyrrolidin-1-yl)benzoate (300 mg, 11.28 mmol) (D41), polystyrene bound triphenylphosphine (1.71 g of loading 1.12 mmol/g, 1.92 mmol), and 4-methoxybutan-1-ol (200 mg, 1.92 mmol) in THF (5 ml) was treated dropwise with diethyl azodicarboxylate (0.302 ml, 1.92 mmol). The mixture was stiffed at room temperature for 6 hrs and then filtered. The resin was washed with THF and the filtrate was concentrated and chromatographed on silica gel (elution with ethyl acetate/hexane) to give methyl 3-(4-methoxybutoxy)-5-(2-oxopyrrolidin-1-yl)benzoate (280 mg).

Workup

  1. filtrationfiltered
  2. washThe resin was washed with THF
  3. concentrationthe filtrate was concentrated
  4. customchromatographed on silica gel (elution with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c90ff64f0afe47298322df47bda42909
Source dataset
uspto-grants-2006_01
Patent number
US06992103B2

Reaction notes

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