Ammonium Chloride → 3-Ethynyl-1-iodooct-1-en-3-ol

HRID 1973162Notes

Reaction equation

HRID 1973162 reaction equation
[I:1][CH:2]=[CH:3][C:4](=[O:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:11]([Mg]Br)#[CH:12].[Cl-].[NH4+]>O1CCCC1>[C:11]([C:4]([OH:10])([CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:3]=[CH:2][I:1])#[CH:12]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 534008741-Iodooct-1-en-3-oneHCID 178418486HCID 178418486, compound

Product 1

HCID 541145263-Ethynyl-1-iodooct-1-en-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.9 g. of 1-iodo-1-octen-3-one in 30 ml. of tetrahydrofuran is added dropwise over 10 minutes to an ice-cooled solution of ethynyl magnesium bromide (prepared from 21 ml. of 3M methyl magnesium bromide in ether and excess acetylene) in 170 ml. of tetrahydrofuran. After stirring at 0° for 1 hour under nitrogen, the mixture is added to ammonium chloride solution and extracted with ether. The extract is washed, dried, evaporated and the residue distilled to obtain the title product, 5.05 g., b.p. 55°-65°/.005 mm.

Workup

  1. extractionextracted with ether
  2. washThe extract is washed
  3. customdried
  4. customevaporated
  5. distillationthe residue distilled

Sources & evidence

ORD record
ord-57f8b0b6aa514676b72c2eb70be900f3
Source dataset
uspto-grants-1976_12
Patent number
US03996255

Reaction notes

Loading…