3-Butyn-1-OL → HCID 68418335, compound

HRID 2067266Notes

Reaction equation

HRID 2067266 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:20])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH3:19])=[O:11])[CH:9]=1)=[N+:2]=[N-:3].[CH2:21]([OH:25])[CH2:22][C:23]#[CH:24].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].CCOC(C)=O.O>C(O)C.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Br:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]([C:8]2[CH:9]=[C:4]([N:1]3[CH:24]=[C:23]([CH2:22][CH2:21][OH:25])[N:3]=[N:2]3)[CH:5]=[CH:6][C:7]=2[CH3:20])=[O:11])=[C:13]([CH3:19])[CH:14]=1

Participants

8

Reactant 4

HCID 135663-Butyn-1-OLHCID 22728543Water ethylacetateHCID 23667548Sodium AscorbateHCID 86605535HCID 86605535, compound

Product 1

HCID 68418335HCID 68418335, compound

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound 451 (170 mg, 0.51 mmol) in ethanol (2 mL) was added but-3-yn-1-ol (39 μL, 0.51 mmol). A freshly prepared solution of copper(II) sulphate pentahydrate (5.0 mg, 0.020 mmol) and sodium ascorbate (20 mg, 0.10 mmol) in water (0.5 mL) was added to the reaction mixture. The flask was closed and stirred for 24 h at RT under argon. The reaction mixture was poured into a mixture of EtOAc/water. The organic phase was washed with water, brine and then dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The crude product was purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) 40:60 to 95:5 as the eluent to afford the title compound as white syrup.

Workup

  1. customThe flask was closed
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThe crude product was purified by continuous gradient flash chromatography

Sources & evidence

ORD record
ord-30a0df4645bf4ec0becf9f12ee16cff0
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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