Ammonium Chloride → HCID 86743960, compound

HRID 1651371Notes

Reaction equation

HRID 1651371 reaction equation
[C:1]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH3:12])(=[O:4])[C:2]#[CH:3].C([Li])CCC.[CH3:18][O:19][C:20]1[CH:29]=[CH:28][C:23]([CH:24]=[CH:25][CH:26]=[O:27])=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1>[OH:27][CH:26](/[CH:25]=[CH:24]/[C:23]1[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:29][CH:28]=1)[C:3]#[C:2][C:1]([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH3:12])=[O:4]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2309953-(4-Methoxyphenyl)prop-2-enalHCID 23050500HCID 23050500, compoundHCID 178418339Butyllithium

Product 1

HCID 86743960HCID 86743960, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.75 g (10.2 mmol) of 2-(2-methoxyethoxy)ethyl propiolate in 20 ml of tetrahydrofuran was treated at -78° under argon with 7 ml of n-butyllithium solution (1.6M in hexane). The mixture was stirred at -78° for 5 minutes and then a solution of 1.65 g (10.2 mmol) of 4-methoxycinnamaldehyde in 25 ml of tetrahydrofuran was added within 10 minutes. The reaction mixture was stirred at -78° for 5 minutes and then treated with 50 ml of saturated ammonium chloride solution. The aqueous phase was extracted twice with ether. The combined organic phases were washed with water, dried over sodium sulphate, filtered and concentrated. Flash chromatography of the residue on 120 g of silica gel (elution agent methylene chloride/ether 4:1) yielded 2-(2-methoxyethoxy)ethyl (E)-4-hydroxy-6-(4-methoxyphenyl)-5-hexen-2-ynoate as a yellow oil.

Workup

  1. stirringThe reaction mixture was stirred at -78° for 5 minutes
  2. extractionThe aqueous phase was extracted twice with ether
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2cf5cd5f95264b70acd413acfbb367d1
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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