HCID 18630369, compound → HCID 18630140, compound

HRID 376701Notes

Reaction equation

HRID 376701 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-695ff6daffdb44248353e969d635f4c9
Source dataset
uspto-grants-2000_02
Patent number
USRE036562

Reaction notes

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