Tetrahydrofuran → HCID 14054080, compound

HRID 973968Notes

Reaction equation

HRID 973968 reaction equation
[CH2:1]([OH:5])[C:2]#[C:3][CH3:4].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([CH3:20])([CH3:19])[CH2:15]C(Cl)=O)=[CH:9][CH:8]=1.[O:21]1CCC[CH2:22]1>CN(C)C1C=CN=CC=1>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]([C:14]([CH3:15])([CH3:19])[CH3:20])[C:22]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[O:21])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 129912-Butyn-1-olHCID 86745224HCID 86745224, compound

Product 1

HCID 14054080HCID 14054080, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 2.43 ml 0.0325 mol) but-2-yn-1-ol and 3.97 g (0.0325 mol of 4-dimethylaminopyridine in 35 ml tetrahydrofuran is added dropwise, at 0°-5° C., a solution of 7.95 g 0.0325 mol 2-(4-chlorophenyl-3,3-dimethylbutyryl chloride in 25 ml tetrahydrofuran. The reaction mixture was allowed to warm to room temperature and after one and a half hours worked up as follows: after removal of the tetrahydrofuran in vacuo, it was treated with water and stirred with ether, the ether phase was dried over magnesium sulphate and concentrated in vacuo. A colourless oil was obtained.

Workup

  1. customafter removal of the tetrahydrofuran in vacuo, it
  2. additionwas treated with water
  3. dry with materialthe ether phase was dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customA colourless oil was obtained

Sources & evidence

ORD record
ord-055be7d36ea34b998a8f97432033e77c
Source dataset
uspto-grants-1991_11
Patent number
US05066675

Reaction notes

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