Propargyl bromide → HCID 56683828, compound

HRID 1469189Notes

Reaction equation

HRID 1469189 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C@H:7]2[C@H:12]([OH:13])[C@@H:11]([OH:14])[C@H:10]([OH:15])[C@@H:9]([CH2:16][OH:17])[O:8]2)=[CH:4][C:3]=1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1.[CH2:26](Br)[C:27]#[CH:28].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[Cl:1][C:2]1[S:6][C:5]([C@H:7]2[C@H:12]([OH:13])[C@@H:11]([OH:14])[C@H:10]([OH:15])[C@@H:9]([CH2:16][OH:17])[O:8]2)=[CH:4][C:3]=1[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:28][C:27]#[CH:26])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10796Cesium carbonateHCID 56670358HCID 56670358, compound

Product 1

HCID 56683828HCID 56683828, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of phenol 29 (124 mg, 0.320 mmol) in acetone (10 mL) were added propargyl bromide (80 wt % in toluene, 1.7 g, 11.2 mmol) and Cs2CO3 (1.5 g, 11.2 mmol) at room temperature. The mixture was stirred at 50° C. for 20 hours. The reaction mixture was cooled to room temperature and filtered off through celite. The filtrate was concentrated in vacuo. The residue was purified by prep HPLC (C18) to provide the title compound 30 (51 mg, 38%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered off through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-e714a57d02a94a68b962a1439b61b1da
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

Loading…