Hydrochloric Acid → HCID 54323931, compound

HRID 1885821Notes

Reaction equation

HRID 1885821 reaction equation
[CH2:1]1COC[CH2:2]1.C([Mg]Cl)=C.[Cl:10][C:11]1[C:18]([CH:19]([CH3:21])[CH3:20])=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=[O:14].Cl>C#C>[Cl:10][C:11]1[C:18]([CH:19]([CH3:21])[CH3:20])=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]([OH:14])[C:1]#[CH:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14997925HCID 14997925, compoundHCID 178461836HCID 178461836, compound

Product 1

HCID 54323931HCID 54323931, compound

Reagents, catalysts & solvents 1

HCID 6326AcetyleneSolvent2×

Conditions

Temperature
0 °C

Procedure

30 ml of absolute THF is saturated under a nitrogen blanket at from 0°-10° C. with acetylene. While passing in further acetylene, 81.7 ml of vinylmagnesium chloride solution (1.47 molar) is dripped in and the mixture is stirred for 30 minutes at 0° C. Subsequently, 18.5 g of 2-chloro-3-isopropylbenzaldehyde is dripped in. The mixture is stirred for 15 hours at room temperature and then poured into 300 ml of ice water. The mixture is acidified with dilute hydrochloric acid and extracted by shaking three times with ether. The combined ether extracts are washed with water, dried and concentrated. There is obtained 22 g of crude product. Purification by column chromatography over silica gel with toluene/acetone (95/%) as eluant gives 9 g of the desired compound.

Workup

  1. customat from 0°-10° C.
  2. stirringThe mixture is stirred for 15 hours at room temperature
  3. extractionextracted
  4. stirringby shaking three times with ether
  5. washThe combined ether extracts are washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThere is obtained 22 g of crude product
  9. customPurification by column chromatography over silica gel with toluene/acetone (95/%) as eluant

Sources & evidence

ORD record
ord-6c028156330547e599826beb053a1895
Source dataset
uspto-grants-1992_09
Patent number
US05147645

Reaction notes

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