Ammonium Chloride → HCID 20145559, compound

HRID 648676Notes

Reaction equation

HRID 648676 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[O:5]=[CH:6][CH:7]([CH3:12])[CH2:8][C:9]#[C:10][CH3:11].[Cl-].[NH4+]>O1CCCC1>[OH:5][CH:6]([CH:7]([CH3:12])[CH2:8][C:9]#[C:10][CH3:11])[C:1]#[CH:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 20145490HCID 20145490, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 20145559HCID 20145559, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 50 ml of 2M ethylmagnesium bromide in tetrahydrofuran at 0° C. was added a solution of 1-oxo-2-methylhex-4-yne in 20 ml of tetrahydrofuran. The mixture was stirred for 11/2 hour at 0° C., poured into saturated ammonium chloride solution, and extracted three times with diethyl ether. The combined extracts were washed with brine, dried over anhydrous sodium sulfate and solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with 20% ethyl acetate in hexane, to give 6.0 g of 3-hydroxy-4-methyloct-1,6-diyne, the compound of formula (LXV).

Workup

  1. extractionextracted three times with diethyl ether
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate and solvent
  4. customremoved under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-30e959ead8654f209c278b824e62291e
Source dataset
uspto-grants-1988_04
Patent number
US04735966

Reaction notes

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