Bis(4-nitrophenyl) carbonate → HCID 15343685, compound

HRID 1893653Notes

Reaction equation

HRID 1893653 reaction equation
[OH:1][C@H:2]1[CH2:6][CH2:5][O:4][CH2:3]1.[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17](=O)[O:18]C2C=CC([N+]([O-])=O)=CC=2)=[CH:12][CH:11]=1)([O-:9])=[O:8]>C(Cl)Cl.O>[O:4]1[CH2:5][CH2:6][CH:2]([O:1][C:17](=[O:18])[O:16][C:13]2[CH:12]=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:15][CH:14]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 78756Bis(4-nitrophenyl) carbonateHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

Product 1

HCID 15343685HCID 15343685, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(S)-(+)-3-Hydroxy-tetrahydrofuran (0.88 mL, 13 mmol) was dissolved in DCM (5 mL) and H2O (40 mL), carbonic acid bis-(4-nitro-phenyl) ester (5.8 g 19 mmol) and TEA (2.8 mL, 20 mmol) were added slowly. The reaction was allowed to stir at room temperature for 24 h. After concentrated, diluted with EtOAc, washed with brine and H2O, dried over Na2SO4, the crude product was purified on silica (12 g, 25-75% EtOAc/hexanes) to give carbonic acid 4-nitro-phenyl ester tetrahydro-furan-3-yl ester as light yellow solid (2.3 g, 71%).

Workup

  1. concentrationAfter concentrated
  2. additiondiluted with EtOAc
  3. washwashed with brine and H2O
  4. dry with materialdried over Na2SO4
  5. customthe crude product was purified on silica (12 g, 25-75% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a7e4fc39f3b7488d856e1dedd6878130
Source dataset
uspto-grants-2013_08
Patent number
US08513186B2

Reaction notes

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