3-Butyn-1-OL → HCID 68420453, compound

HRID 2067278Notes

Reaction equation

HRID 2067278 reaction equation
[N:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:20])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[Cl: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[Cl:20])=[O:11])=[C:13]([Cl:19])[CH:14]=1

Participants

8

Reactant 4

HCID 135663-Butyn-1-OLHCID 22728543Water ethylacetateHCID 23667548Sodium AscorbateHCID 86605537HCID 86605537, compound

Product 1

HCID 68420453HCID 68420453, compound

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound 455 (1.32 g, 3.56 mmol) in ethanol (20 mL) was added but-3-yn-1-ol (0.3 mL, 3.91 mmol). A freshly prepared solution of copper(II) sulphate pentahydrate (36 mg, 0.14 mmol) and sodium ascorbate (141 mg, 0.71 mmol) in water (3.2 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-52e366aac2de4937b3b1c5ef8e6f805f
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

Loading…