Ethyl Bromide → HCID 22759318, compound

HRID 460847Notes

Reaction equation

HRID 460847 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-fluorophenoxy-acetaldehyde (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-7c743f7eab3a4edb90280485f0b1b5f1
Source dataset
uspto-grants-1977_12
Patent number
US04061643

Reaction notes

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