Water → Prop-2-yn-1-yl benzoate

HRID 2401331Notes

Reaction equation

HRID 2401331 reaction equation
[CH2:1](O)[C:2]#[CH:3].C(Cl)Cl.CCN(CC)CC.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH2:24]>CN(C1C=CN=CC=1)C>[C:15]([O:22][CH2:3][C:2]#[CH:1])(=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 7859Propargyl alcoholHCID 8471Triethylamine

Product 1

HCID 336291Prop-2-yn-1-yl benzoate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of prop-2-yn-1-ol (3.63 mL, 62.4 mmol), DCM (180 mL), and Et3N (17.40 mL, 125 mmol) at 0° C. were added benzoyl chloride (7.25 mL, 62.4 mmol) and DMAP (0.381 g, 3.12 mmol). The reaction was stirred while warming to room temperature overnight. The reaction was diluted with water and the layers separated. The aqueous was extracted with DCM and the combined organics were dried over Na2SO4, filtered, and concentrated to afford prop-2-yn-1-yl benzoate which was used in subsequent reactions without further purification. LC/MS m/z 161 [M+H]+.

Workup

  1. customthe layers separated
  2. extractionThe aqueous was extracted with DCM
  3. dry with materialthe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d977b2d89431403f8dfe35413140fc84
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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