Sodium Hydroxide → HCID 19602326, compound

HRID 1604238Notes

Reaction equation

HRID 1604238 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[C:7]2[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=2S[C:10]=1[Si:11]([CH3:14])([CH3:13])[CH3:12])=[O:5])[CH3:2].ClC1C=C(C=CC=1)C(OO)=O.[S:30](S([O-])=O)([O-:33])(=O)=[O:31].[Na+].[Na+].[OH-].[Na+]>C(Cl)Cl.[Cl-].[Na+].O>[CH2:1]([NH:3][C:4]([C:6]1[C:7]2[CH:8]=[CH:15][CH:16]=[CH:17][C:18]=2[S:30](=[O:33])(=[O:31])[C:10]=1[Si:11]([CH3:13])([CH3:12])[CH3:14])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 19602331HCID 19602331, compound

Product 1

HCID 19602326HCID 19602326, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of the product of Example 8 (0.6 g, 2.2 mmol) and 1 g of 80-85% 3-chloroperoxybenzoic acid in 16 mL methylene chloride was refluxed for 2 h, then cooled and diluted with additional methylene chloride. The solution was treated sequentially with sat sodium metabisulfite, 1.25N NaOH, and brine; then dried and concentrated in vacuo. Flash chromatography of the residue with 35% ethyl acetate-hexane gave 0.5 g of the desired product as a white solid, a yield of 74.5%. m.p. 135-148° C.

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturecooled
  3. customthen dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48a650f7eb8d41d4996e8be21e56e0e1
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Reaction notes

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