Diethyl Ether → HCID 19917052, compound

HRID 1756164Notes

Reaction equation

HRID 1756164 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[C:4]#[C:5][CH2:6][OH:7].Br[CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:21]=[CH:20][S:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1.C(OCC)C>CN(C)C=O.O>[S:19]1[CH:20]=[CH:21][C:17]([C:13]2[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=2)[CH2:10][O:7][CH2:6][C:5]#[C:4][CH2:3][OH:8])=[CH:18]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 80662-Butyne-1,4-diolHCID 24758Sodium hydrideHCID 132459263-[3-(Bromomethyl)phenyl]thiophene

Product 1

HCID 19917052HCID 19917052, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

Under a nitrogen atmosphere, 0.47 g of 60% oily sodium hydride was suspended in 10 ml of dimethylformamide, and a dimethylformamide solution (10 ml) of 1.0 g of 2-butyn-1,4-diol was added dropwise with stirring and ice cooling. After the mixture was stirred for 10 minutes, a dimethylformamide solution (5 ml) of 0.59 g of 3-(3-bromomethylphenyl)thiophene was added. The mixture was stirred at room temperature for 1 hour and then ethyl ether and water were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [hexane/ethyl acetate=3/1] to give 0.48 g of 4-[3-(3-thienyl)benzyloxy]-2-butyn-1-ol as a colorless oil.

Workup

  1. stirringAfter the mixture was stirred for 10 minutes
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. customThe organic layer separated
  4. customthe product was purified by silica gel column chromatography [hexane/ethyl acetate=3/1]

Sources & evidence

ORD record
ord-edb614459823463e9b499ac11368adc7
Source dataset
uspto-grants-1995_08
Patent number
US05439932

Reaction notes

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