Tetrahydrofuran → HCID 178455786, compound

HRID 371801Notes

Reaction equation

HRID 371801 reaction equation
C([Li])CCC.[CH3:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9].O1CCCC1.[CH2:18]([C@H:20]1[CH2:25][CH2:24][C@H:23]([C:26](OCC)=[O:27])[CH2:22][CH2:21]1)[CH3:19]>CCCCCC>[O:27]=[C:26]([C@H:23]1[CH2:24][CH2:25][C@H:20]([CH2:18][CH3:19])[CH2:21][CH2:22]1)[CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 12958Dimethyl methylphosphonateHCID 178418339ButyllithiumHCID 178472358HCID 178472358, compound

Product 1

HCID 178455786HCID 178455786, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

Under an atmosphere of nitrogen, 47 ml. of a 1.25M solution of n-butyllithium in n-hexane were added dropwise to a solution of 7.64 g. of dimethyl methylphosphonate in 120 ml. of tetrahydrofuran at -70° C. After one hour of stirring at -70° C., a solution of 5.63 g. of ethyl trans-4-ethylcyclohexanecarboxylate [c.f. N. L. Allinger and L. A. Freiberg, J. Org. Chem., 31, 894, (1966)] in 30 ml. of tetrahydrofuran was added dropwise at -70° C., and the mixture was stirred at the same temperature for one hour and further stirred at -5° C., for one hour. The reaction mixture was then acidified with acetic acid and concentration under reduced pressure. The residue was diluted with diethyl ether, washed with water and an aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by distillation to give 5.0 g. of the title compound having the following physical characteristics:-

Workup

  1. customat -70° C
  2. stirringthe mixture was stirred at the same temperature for one hour
  3. stirringfurther stirred at -5° C., for one hour
  4. concentrationThe reaction mixture was then acidified with acetic acid and concentration under reduced pressure
  5. additionThe residue was diluted with diethyl ether
  6. washwashed with water
  7. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulphate
  8. concentrationconcentrated under reduced pressure
  9. distillationThe residue was purified by distillation
  10. customto give 5.0 g

Sources & evidence

ORD record
ord-bdc99ff754f245b49d0913e748d5e79f
Source dataset
uspto-grants-1978_05
Patent number
US04087620

Reaction notes

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