Phenylacetylene → HCID 57779447, compound

HRID 509182Notes

Reaction equation

HRID 509182 reaction equation
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[N-:14]=[N+:15]=[N-:16].[Na+].CS(C)=O.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[C:35]1([C:41]#[CH:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>[Cl-].[Na+].O.S([O-])([O-])(=O)=O.[Cu+2].O>[C:8]1([CH:2]([N:14]2[CH:42]=[C:41]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:16]=[N:15]2)[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 10821PhenylacetyleneHCID 97780Ethyl bromophenylacetateHCID 23667548Sodium AscorbateHCID 86632440HCID 86632440, compound

Product 1

HCID 57779447HCID 57779447, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of ethyl 2-bromo-2-phenylacetate 21 (1.60 g, 6.58 mmol) in sodium azide/DMSO solution (0.5 M, 13.16 mL, 6.58 mmol) which had been stirred at room temperature for 1 h was added water (10 mL), sodium ascorbate (0.130 g, 0.658 mmol), phenylacetylene (0.723 mL, 6.58 mmol) and aq. copper(II) sulfate solution (1.0 M, 1.30 mL, 1.30 mmol) (in that order). The reaction mixture was stirred for 16 h. Brine was added and extraction with ethyl acetate. The organic layer was dried over Na2SO4, filtered, and concentrated. The crude material was purified by silica gel column chromatography with gradient of ethyl acetate (0-50%) in hexane to afford compound (24) as a light yellow solid (1.31 g, 65%). LRMS: calc. 307.4, found 308.4 (MH)+.

Workup

  1. extractionextraction with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel column chromatography with gradient of ethyl acetate (0-50%) in hexane

Sources & evidence

ORD record
ord-46c1157c478b41429391923266b8c5aa
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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