Ammonium Chloride → 2H-Pyran, tetrahydro-2-(7-octyn-1-yloxy)-

HRID 892996Notes

Reaction equation

HRID 892996 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]Br.[CH2:15](N)[CH2:16]N.[C-]#[C-].[Li+].[Li+].[Cl-].[NH4+]>>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:15]#[CH:16]

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 1038602-[(6-bromohexyl)oxy]tetrahydro-2H-pyranHCID 178511344HCID 178511344, compound

Product 1

HCID 860502H-Pyran, tetrahydro-2-(7-octyn-1-yloxy)-

Procedure

6-[(Tetrahydropyran-2-yl)oxy]-1bromohexane (2.0 g) is added, with a mild exotherm, to a stirred mixture of lithium acetylide ethylenediamine (4.9 g) at 20°-25°. The mixture is stirred overnight, then is poured into ice and aqueous ammonium chloride and extracted with ether/pentane. The extracts are dried over magnesium sulfate and concentrated to give the title compound, NMR (CDCl3) 1.3-2.5, 3.3-4.1 and 4.7 δ.

Workup

  1. extractionextracted with ether/pentane
  2. dry with materialThe extracts are dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fdce72dd1ad34b87a931e477a02f8345
Source dataset
uspto-grants-1992_06
Patent number
US05120843

Reaction notes

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