Water → HCID 178473696, compound

HRID 582178Notes

Reaction equation

HRID 582178 reaction equation
[CH2:1]([O:3][C:4]([S-:6])=[S:5])[CH3:2].[K+].[PH:8](=[O:11])([OH:10])[OH:9].[CH2:12]([C:14]([CH2:42][CH3:43])([CH:16](Br)[C:17]1[N:21]=[CH:20][N:19]([C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1)[CH3:15])[CH3:13].O>O1CCCC1.C1OCCOCCOCCOCCOCCOC1>[PH:8](=[O:9])([OH:11])[OH:10].[CH2:42]([C:14]([CH2:12][CH3:13])([CH:16]([S:5][C:4]([O:3][CH2:1][CH3:2])=[S:6])[C:17]1[N:21]=[CH:20][N:19]([C:22]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:18]=1)[CH3:15])[CH3:43]

Participants

6

Reactant 3

HCID 962WaterHCID 2735045Potassium ethylxanthateHCID 178442503HCID 178442503, compound

Product 1

HCID 178473696HCID 178473696, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 18-Crown-6 (0.03 g) in dry tetrahydrofuran (25 ml) was treated successively with potassium ethylxanthate (0.44 g) and diethyl 3-bromo-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.0 g, prepared as described in Example 29). The mixture was allowed to stand for two days, poured into water and extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulphate, and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ethanol (49:1) as eluant, to give diethyl 3(ethoxythiocarbonylthio)-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.86 g) as a colourless gum. NMR(CDCl3): δ 1.25(6H,m), 1.4(3H,t), 1.7-1.9(2H,m), 2.3-2.4(2H,m), 4.0(4H,m), 4.6(2H,m), 5.05(1H,t), 7.1(6H,m), 7.3(9H,m), 7.9(1H,S). M/S: M+ 609.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-3662c22e648b423788badc57610c3d2a
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

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