Ammonia → 7-Chloro-1-(2-furyl)-1-methoxy-3-heptyne

HRID 1032507Notes

Reaction equation

HRID 1032507 reaction equation
[NH2-].[Li+].N.[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH:9]([O:13][CH3:14])[CH2:10][C:11]#[CH:12].Br[CH2:16][CH2:17][CH2:18][Cl:19]>O1CCCC1>[Cl:19][CH2:18][CH2:17][CH2:16][C:12]#[C:11][CH2:10][CH:9]([C:5]1[O:4][CH:8]=[CH:7][CH:6]=1)[O:13][CH3:14]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 80061-Bromo-3-chloropropaneHCID 24532Lithium amideHCID 147744234-(2-Furyl)-4-methoxy-1-butyne

Product 1

HCID 147744247-Chloro-1-(2-furyl)-1-methoxy-3-heptyneYield 67.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 0.51 g of lithium amide and 25 ml of liquid ammonia was added a solution of 3.0 g of 4-(2-furyl)-4-methoxy-1-butyne in 2.5 ml of tetrahydrofuran. The mixture was stirred under reflux for 30 minutes and then treated with a solution of 3.94 g of 1-bromo-3-chloropropane in 5 ml of tetrahydrofuran. This mixture was stirred under reflux for one hour, then the ammonia was allowed to evaporate and the residue partitioned with ether and water. The ether layer was separated and evaporated. The residue was distilled at 0.06 mm on a Kugelrohr, giving 3.07 g of the desired compound as an oil, bp 110°-120° C.

Workup

  1. temperatureunder reflux for 30 minutes
  2. stirringThis mixture was stirred
  3. temperatureunder reflux for one hour
  4. customto evaporate
  5. customthe residue partitioned with ether and water
  6. customThe ether layer was separated
  7. customevaporated
  8. distillationThe residue was distilled at 0.06 mm on a Kugelrohr

Sources & evidence

ORD record
ord-70d5c32f15394c67a26758ea08c236b8
Source dataset
uspto-grants-1990_09
Patent number
US04958037

Reaction notes

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