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

HRID 2405803Notes

Reaction equation

HRID 2405803 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-284de38154df4a7e8099e7a7f983ae1b
Source dataset
uspto-grants-2014_08
Patent number
US08809267B2

Reaction notes

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