HCID 10160091, compound → HCID 86760585, compound

HRID 1594500Notes

Reaction equation

HRID 1594500 reaction equation
CO[C:3]1[C:8](OC)=[CH:7][C:6]([CH:11]([O:18]C(=O)C(Cl)(Cl)Cl)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:5]([N+:25]([O-:27])=O)[CH:4]=1.CN(C)C1C=CC([N+]([O-])=O)=C([CH:39]([O:46]C(=O)C(Cl)(Cl)Cl)C2C=CC=CC=2)C=1[N+]([O-])=O>ClCCl>[CH3:39][O:46][C:15]1[CH:14]=[CH:13][C:12]([C:11](=[O:18])[C:6]2[CH:7]=[CH:8][CH:3]=[CH:4][C:5]=2[N:25]=[O:27])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 10160091HCID 10160091, compoundHCID 10161825HCID 10161825, compound

Product 1

HCID 86760585HCID 86760585, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Esters 39 and 40, 2% solution in dichloromethane (3.5 mL), and ester 43, 0.25% solution in dichloromethane (3.5 mL), were irradiated in the photoreactor at 350 nm for 200 minutes. The degree of photoconversion could be conveniently monitored by TLC. Each solution was concentrated to a half of its volume and applied onto a column of silicagel (4 g, Coarse silicagel). The column was eluted with CH2Cl2, appropriate fractions were combined and the solvent was removed in vacuo. The residue was dissolved in water/ethanol (1:1) (2 mL) and freeze-dried to give the photoproduct.

Workup

  1. concentrationEach solution was concentrated to a half of its volume
  2. washThe column was eluted with CH2Cl2, appropriate fractions
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in water/ethanol (1:1) (2 mL)
  5. customfreeze-dried
  6. customto give the photoproduct

Sources & evidence

ORD record
ord-aaceed8d2b6143b99ca42336691464f3
Source dataset
uspto-grants-2007_11
Patent number
US07301049B2

Reaction notes

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