3-Butyn-1-OL → HCID 69606498, compound

HRID 2067296Notes

Reaction equation

HRID 2067296 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[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[CH3:20])=[O:11])=[C:13]([Cl:19])[CH:14]=1

Participants

8

Reactant 4

HCID 135663-Butyn-1-OL2×HCID 22728543Water ethylacetateHCID 23667548Sodium Ascorbate2×HCID 86605542HCID 86605542, compound

Product 1

HCID 69606498HCID 69606498, compound

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalyst2×HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of compound 470 (1.04 g, 2.97 mmol) in ethanol (18 mL) was added but-3-yn-1-ol (225 μL, 2.97 mmol), copper(II) sulphate pentahydrate (30 mg, 0.12 mmol) and a solution of sodium ascorbate (119 mg, 0.6 mmol) in water (3.0 mL). The flask was closed and stirred for 24 h at RT under argon. After 18 h was added but-3-yn-1-ol (225 μL, 2.97 mmol), copper(II) sulphate pentahydrate (30 mg, 0.12 mmol) and a solution of sodium ascorbate (119 mg, 0.6 mmol) in water (3.0 mL). After 2 h 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 flash chromatography using EtOAc/petroleum ether (40-60) 3:1 as the eluent to afford the title compound as offwhite solid.

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 flash chromatography

Sources & evidence

ORD record
ord-2dc3047532dd4d8b95e3751a929f9ffa
Source dataset
uspto-grants-2012_10
Patent number
US08293772B2

Reaction notes

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