Triethyl phosphite → HCID 68592275, compound

HRID 898842Notes

Reaction equation

HRID 898842 reaction equation
[C:1]1(/[CH:7]=[CH:8]\[CH2:9][O:10][C:11](=[O:22])[C:12](=[N+]=[N-])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(OCC)(OCC)OCC>C1(C)C=CC=CC=1.[Cu]I>[C:16]([O:15][C:13]([C@:12]12[C@@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C@H:8]1[CH2:9][O:10][C:11]2=[O:22])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 31215Triethyl phosphiteHCID 86607496HCID 86607496, compound

Product 1

HCID 68592275HCID 68592275, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

To the 2-diazomalonic acid t-butyl ester (Z)-3-phenyl-allyl ester (16 g, 54 mmol) above were added triethyl phosphite (0.090 g, 0.54 mmol) and copper (I) iodide (0.10 g, 0.54 mmol) in toluene (490 mL). After heating at 130° C. for 5 hours, the solid was filtered off and the filtrate was concentrated. The reaction mixture was purified by column chromatography using dichloromethane as an eluent. Purification afforded 5.2 g of the desired diastereomer and 2.8 g of the other diastereomer.

Workup

  1. filtrationthe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe reaction mixture was purified by column chromatography
  4. customPurification
  5. customafforded 5.2 g of the desired diastereomer and 2.8 g of the other diastereomer

Sources & evidence

ORD record
ord-f64458128f924589817a995ac4dacce0
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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