Water → Prop-2-yn-1-yl benzoate

HRID 1772317Notes

Reaction equation

HRID 1772317 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. m/z (ESI) 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-19f5b54e74e54989a5603cae9ab85787
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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