Tetrahydrofuran → HCID 67805153, compound

HRID 1679620Notes

Reaction equation

HRID 1679620 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH:8]=[CH:9][C:10](Cl)=[O:11].O1CCC[CH2:20]1.C[Mg]Br>C1(C)C=CC=CC=1>[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH:8]=[CH:9][C:10](=[O:11])[CH3:20]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 131711059HCID 131711059, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67805153HCID 67805153, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-30 °C

Procedure

10.0 g. (0.039 mole) of crude acid chloride from Example 5, Step (c), is dissolved in 200 ml. of dry tetrahydrofuran and the solution placed in a 500 ml. round bottom flask fitted with a septum inlet and magnetic stirrer, and held under a nitrogen atmosphere. The solution is cooled to -30° C. in a dry ice/isopropanol bath and 19.5 ml (0.039 mole) of a commercial 2M methyl magnesium bromide solution in dry toluene is added, dropwise, over 30 minutes. After the addition is complete, the mixture is allowed to warm to room temperature and then stirred for 1 hour. The reaction is quenched by the addition of 20 ml. of saturated ammonium chloride solution and the organic layer is separated. The aqueous layer is extracted twice with 20 ml. portions of ether and the combined organic extracts are then dried over anhydrous magnesium sulphate and evaporated to yield the heading compound, m.p. 130° to 133° C., after recrystallization from petroleum ether.

Workup

  1. customround bottom flask fitted with a septum inlet and magnetic stirrer
  2. additionAfter the addition
  3. temperatureto warm to room temperature
  4. customThe reaction is quenched by the addition of 20 ml
  5. customof saturated ammonium chloride solution and the organic layer is separated
  6. extractionThe aqueous layer is extracted twice with 20 ml
  7. dry with materialportions of ether and the combined organic extracts are then dried over anhydrous magnesium sulphate
  8. customevaporated
  9. customto yield the heading compound, m.p. 130° to 133° C.
  10. customafter recrystallization from petroleum ether

Sources & evidence

ORD record
ord-50bae6c759b2459083376239fb617794
Source dataset
uspto-grants-1978_03
Patent number
US04081476

Reaction notes

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