Ammonium Chloride → HCID 20033707, compound

HRID 231688Notes

Reaction equation

HRID 231688 reaction equation
[CH3:1][Mg]Br.[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]2[S:14][CH:15]=[CH:16][C:17]=2[CH:18]=[O:19])=[CH:8][CH:7]=1.[NH4+].[Cl-]>CCOCC.O>[OH:19][CH:18]([C:17]1[CH:16]=[CH:15][S:14][C:13]=1[S:12][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH3:4])=[CH:11][CH:10]=1)[CH3:1]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 20033696HCID 20033696, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 20033707HCID 20033707, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of methylmagnesium bromide (20.7 ml, 0.06 mol of 2.9M solution in ether) in anhydrous ether (50 ml) cooled to -5° C. was added 2-(4-methoxyphenylthio)thiophene 3-carboxaldehyde (10.0 g, 0.04 mol) in anhydrous ether (40 ml) over a 1/2 hour period under nitrogen atmosphere. The mixture was stirred at 0° C. for 2 hours and was decomposed by adding a solution of NH4Cl (5.3 g, 0.1 mol) in water (50 ml) over a 20 minute period at 0° to 15° C. The ether layer was separated, washed with 3NHCl, saturated, NaHCO3 and water. It was dried, filtered and concentrated in vacuo at room temperature to obtain an amber oil. The product was purified by silica gel column chromatography using 50/50 hexane-ethyl acetate. This procedure gave 8.8 g of amber oil. Yield was 83%.

Workup

  1. customThe ether layer was separated
  2. washwashed with 3NHCl, saturated, NaHCO3 and water
  3. customIt was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo at room temperature
  6. customto obtain an amber oil
  7. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b352abd9c3664c7ab0d5a59bb3bb21f4
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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