Ethyl Bromide → HCID 22759318, compound

HRID 1730129Notes

Reaction equation

HRID 1730129 reaction equation
[Mg].BrCC.[CH2:5]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)[C:6]#[CH:7].[F:15][C:16]1[CH:25]=[CH:24][C:19]([O:20][CH2:21][CH:22]=[O:23])=[CH:18][CH:17]=1.[Cl-].[NH4+]>O1CCCC1.O>[O:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[O:8][CH2:5][C:6]#[C:7][CH:22]([OH:23])[CH2:21][O:20][C:19]1[CH:24]=[CH:25][C:16]([F:15])=[CH:17][CH:18]=1

Participants

8

Reactant 5

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 5462224MagnesiumHCID 110518692-(4-Fluorophenoxy)acetaldehyde

Product 1

HCID 22759318HCID 22759318, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To the Grignard reagent prepared from magnesium (12.2 g., 0.5 mole) and bromoethane (54.5 g., 0.5 mole) in tetrahydrofuran (400 ml.) is added, dropwise, during 30 minutes, a solution of tetrahydro-2-(2-propynyloxy)-2H-pyran (67.3 g., 0.5 mole) in tetrahydrofuran (50 ml.). The mixture is stirred at room temperature for 1 hour and then treated, dropwise, during 1 hour with 4-fluorophenoxyacetaldehyde (61.6 g., 0.4 mole). The resulting mixture is heated at reflux for 1 hour, then cooled and poured into an ice-cold saturated solution of ammonium chloride in water.

Workup

  1. additionis added
  2. additiontreated
  3. temperatureThe resulting mixture is heated
  4. temperatureat reflux for 1 hour
  5. temperaturecooled

Sources & evidence

ORD record
ord-e897c1dd18924f1cbe958078f027b8fa
Source dataset
uspto-grants-1976_11
Patent number
US03991106

Reaction notes

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