Ammonium Chloride → HCID 86646563, compound

HRID 1698396Notes

Reaction equation

HRID 1698396 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[C:18]([Mg]Br)#[CH:19].[Cl-].[NH4+]>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]([OH:9])[C:18]#[CH:19])[CH:10]=[CH:11][C:12]=1[N:13]([CH2:16][CH3:17])[CH2:14][CH3:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86042697HCID 86042697, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 86646563HCID 86646563, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 g (6.7 mmol) of 3-tert-butyl-4-diethylamino-benzaldehyde are dissolved in 20 ml of dry THF, under a light nitrogen flow, at 0° C. 17 ml (8.7 mmol) of a 0.5M solution of ethynylmagnesium bromide are added dropwise and the medium is then brought back to ambient temperature and stirred for 30 minutes. The mixture is then poured into a saturated solution of ammonium chloride, extracted with ethyl acetate, dried over sodium sulphate and then concentrated to dryness. The residue is purified by flash chromatography (90/10 heptane/ethyl acetate). 780 mg of 1-(3-tert-butyl-4-diethylaminophenyl)prop-2-yn-1-ol are obtained in the form of a colourless oil (yield=47%).

Workup

  1. customat 0° C
  2. customis then brought back to ambient temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by flash chromatography (90/10 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-db5ea66ca81f4cfa90d6c54c789e1240
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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