4-Methylmorpholine → 3-p-Nitrophenoxycarbonyloxymethyl-2,5-dihydrofuran

HRID 52847Notes

Reaction equation

HRID 52847 reaction equation
[OH:1][CH2:2][C:3]1[CH2:4][O:5][CH2:6][CH:7]=1.CN1CCOCC1.[N+:15]([C:18]1[CH:27]=[CH:26][C:21]([O:22][C:23](Cl)=[O:24])=[CH:20][CH:19]=1)([O-:17])=[O:16]>C(Cl)Cl>[N+:15]([C:18]1[CH:27]=[CH:26][C:21]([O:22][C:23]([O:1][CH2:2][C:3]2[CH2:4][O:5][CH2:6][CH:7]=2)=[O:24])=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 189395793-Hydroxymethyl-2,5-dihydrofuran

Product 1

HCID 189397293-p-Nitrophenoxycarbonyloxymethyl-2,5-dihydrofuranYield 66.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 65 mg (0.65 mmol) of the compound from Example 336D in methylene chloride was added 0.079 mL of 4-methylmorpholine and 144 mg (0.715 mmol) of p-nitrophenoxycarbonylchloride. The mixture was stirred for 2 hours, diluted with solvent, washed with saturated brine, and the solvent removed. The residue was chromatographed on a silica gel column, eluting with 20% and 30% ethyl acetate in hexane. The solvent was removed and the product dried to afford 0.115 g of the title product.

Workup

  1. additiondiluted with solvent
  2. washwashed with saturated brine
  3. customthe solvent removed
  4. customThe residue was chromatographed on a silica gel column
  5. washeluting with 20% and 30% ethyl acetate in hexane
  6. customThe solvent was removed
  7. customthe product dried

Sources & evidence

ORD record
ord-38cba9aae4994a3290da5efa8a4fd6fd
Source dataset
uspto-grants-1997_04
Patent number
US05616714

Reaction notes

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