Sodium Hydroxide → HCID 14418535, compound

HRID 1429290Notes

Reaction equation

HRID 1429290 reaction equation
[CH:1](=[N:8]/[OH:9])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S([N-]Cl)(=O)=O)=CC=1.O.O.O.[Na+].[CH2:26]([Sn:30]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:33][CH2:34][CH2:35][CH3:36])[C:31]#[CH:32])[CH2:27][CH2:28][CH3:29].[OH-].[Na+].[OH-].[NH4+]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].[Cu].O.C(O)CCC>[C:2]1([C:1]2[CH:32]=[C:31]([Sn:30]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH2:35][CH3:36])[O:9][N:8]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

10

Reactant 5

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 517414chloramine-T trihydrateHCID 621176EthynyltributyltinHCID 5324611Benzaldehyde Oxime

Product 1

HCID 14418535HCID 14418535, compound

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 24463Copper sulfate pentahydrateCatalystHCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

(E)-benzaldehyde oxime (Sigma Aldrich; 3.3 g, 20 mmol) in tent butanol and water (1:1) 80 ml, is treated with chloramine T trihydrate (Sigma Aldrich; 5.9 g, 21 mmol) in small, portions over 5 min. The reaction is then treated with copper sulfate pentahydrate (0.15 g, 0.6 mmol) and copper turnings ˜50 mg and tributylethynylstannane (6.3 g, 20 mmol). The reaction is then adjusted to pH 6 with sodium hydroxide solution and stirred for 6 h. The reaction mixture is treated with dilute ammonium hydroxide solution to remove all copper salts. The product is collected by filtration, redissolved in ethyl acetate and filtered through a short plug of silica gel. The filtrate is concentrated in vacuum to give 3-phenyl-5-(tributylstannyl) isoxazole.

Workup

  1. customto remove all copper salts
  2. filtrationThe product is collected by filtration
  3. dissolutionredissolved in ethyl acetate
  4. filtrationfiltered through a short plug of silica gel
  5. concentrationThe filtrate is concentrated in vacuum

Sources & evidence

ORD record
ord-a8476b350a6545c6aa780fbf484c75c4
Source dataset
uspto-grants-2015_01
Patent number
US08940274B2

Reaction notes

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