Cornforth reagent → HCID 57696850, compound

HRID 217629Notes

Reaction equation

HRID 217629 reaction equation
[OH:1][C:2]([CH3:22])([CH3:21])[CH2:3][C@H:4]1[CH2:8][O:7][C@@:6]([C@@H:10]2[C@:18]3([CH3:19])[C@H:13]([C@@H:14]([OH:20])[CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11]2)([CH3:9])[CH2:5]1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[OH:1][C:2]([CH3:22])([CH3:21])[CH2:3][C@H:4]1[CH2:8][O:7][C@@:6]([C@@H:10]2[C@:18]3([CH3:19])[C@H:13]([C:14](=[O:20])[CH2:15][CH2:16][CH2:17]3)[CH2:12][CH2:11]2)([CH3:9])[CH2:5]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 86630344HCID 86630344, compound

Product 1

HCID 57696850HCID 57696850, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 14a (100 mg, 0.32 mmol) in dry CH2Cl2 (10 mL) was treated with PDC (pyridinium dichromate, 0.5 g, 1.3 mmol). The mixture was stirred at room temperature for 20 h, the mixture was filtered and concentrated in vacuum. The residue was purified by flash chromatography (SiO2, 3×5.5 cm, 20% EtOAc-hexanes) to give 1R (90 mg, 91%, white solid, mp: 82° C.).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated in vacuum
  3. customThe residue was purified by flash chromatography (SiO2, 3×5.5 cm, 20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-3735f4451c5d4aac80c24913cbb28e7f
Source dataset
uspto-grants-2012_06
Patent number
US08198263B2

Reaction notes

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