Ammonium Chloride → HCID 11162207, compound

HRID 2241173Notes

Reaction equation

HRID 2241173 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][OH:12])=[CH:5][C:4]=1[O:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18].[CH:19]([Mg]Cl)([CH3:21])[CH3:20].[Cl-].[NH4+]>O1CCCC1.C(OCC)C.O.C(OCC)(=O)C.[Cu]I>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[C:10](\[CH:19]([CH3:21])[CH3:20])/[CH2:11][OH:12])=[CH:5][C:4]=1[O:13][CH2:14][CH2:15][CH2:16][O:17][CH3:18]

Participants

9

Reactant 3

HCID 25517Ammonium ChlorideHCID 24983697HCID 24983697, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 11162207HCID 11162207, compound

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A dried 50 ml Schlenk tube is charged under an argon atmosphere with a solution of 4.034 mmol of 3-[4-methoxy-3-(3-methoxypropoxy)phenyl]prop-2-yn-1-ol in 20 ml of tetrahydrofuran. The solution is admixed with 0.403 mmol of solid copper(I) iodide and the suspension is cooled to 0° C. Subsequently 6.05 ml of a 2.0 molar isopropyl-magnesium chloride solution in diethyl ether are added. The resulting mixture is stirred at 0° C. over 3.5 hours. The reaction mixture is then poured onto saturated aqueous ammonium chloride solution at 0° C. and then diluted with water and ethyl acetate. The phases are separated; the aqueous phase is extracted with ethyl acetate (2×). The combined organic phases are washed with brine, dried over sodium sulphate, filtered and concentrated by evaporation on a rotary evaporator. The title compound A2 is obtained as a yellow oil (967 mg) from the residue by means of flash chromatography (SiO2 60 F, 2:1 ethyl acetate-hexane). Rf=0.48 (2:1 ethyl acetate-heptane); Rt=3.97 (gradient I).

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted with ethyl acetate (2×)
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation on a rotary evaporator

Sources & evidence

ORD record
ord-337e27637ad447ba9230bf3be3b6a831
Source dataset
uspto-grants-2010_05
Patent number
US07723550B2

Reaction notes

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