HCID 18630369, compound → HCID 18630140, compound

HRID 378083Notes

Reaction equation

HRID 378083 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[S:7][C:8]([CH2:15][OH:16])=[CH:9][C:10]=1[Si:11]([CH3:14])([CH3:13])[CH3:12])=[O:5])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[CH2:1]([NH:3][C:4]([C:6]1[S:7][C:8]([CH:15]=[O:16])=[CH:9][C:10]=1[Si:11]([CH3:14])([CH3:13])[CH3:12])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 18630369HCID 18630369, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 18630140HCID 18630140, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the compound of step b (1.3 g, 5 mmol) in 40 mL CH2Cl2 containing 1.8 g celite was added 2.4 g pyridinium chlorochromate and the resulting reaction mixture was stirred at RT for 2 h. The CH2Cl2 solution was filtered through celite, washed with water, brine, dried and concentrated in vacuo. The residue was purified by flash chromatography with 10% ethyl acetate-hexane to give 1.1 g of the desired product as a light yellow solid, m.p. 62-65° C.

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe CH2Cl2 solution was filtered through celite
  3. washwashed with water, brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography with 10% ethyl acetate-hexane

Sources & evidence

ORD record
ord-5fce9952d54f434395394d08d8793c0c
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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