Hexane → HCID 60039216, compound

HRID 898847Notes

Reaction equation

HRID 898847 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]([O:17][C:18]([CH3:21])(C)C)(=[O:16])[CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].ClCC1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)CO1.CCCCCC>C(O)(C)(C)C.O1CCCC1>[C:12]([O:11][C:9]([C@:8]12[CH2:1][C@@:21]1([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:18][O:17][C:7]2=[O:16])=[O:10])([CH3:13])([CH3:14])[CH3:15]

Participants

7

Reactant 4

HCID 8058HexaneHCID 68324Di-tert-butyl malonateHCID 2002042-(Chloromethyl)-2-phenyloxiraneHCID 23665647Potassium tert-butoxide

Product 1

HCID 60039216HCID 60039216, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, potassium t-butoxide (110 g, 0.78 mol) was added to a solution of di-t-butyl malonate (170 g, 0.78 mol) in t-butyl alcohol (1.5 L) in 3 portions at room temperature. After stirring at room temperature for 1 hour, the mixture was heated to 70° C. Then a solution of 2-chloromethyl-2-phenyloxirane (120 g) in tetrahydrofuran (500 mL) synthesized by the method described in J. Org. Chem. (1962, 27, 2241-2243) was added dropwise over 90 min. After stirring for 12 hours at 70° C., the mixture was cooled to room temperature and the solvent was evaporated. 10% Aqueous citric acid solution (500 mL) was added to the residue. The mixture was extracted with ethyl acetate (2.0 L), sequentially washed with water (500 mL) and saturated aqueous sodium chloride solution (200 mL), and dried over magnesium sulfate. After filtration and evaporation, the title compound (120 g, 3 step, yield 54%) was recrystallized from a mixed solution of hexane:diisopropyl ether=1:1 (600 mL) as a white solid.

Workup

  1. temperaturethe mixture was heated to 70° C
  2. addition(1962, 27, 2241-2243) was added dropwise over 90 min
  3. stirringAfter stirring for 12 hours at 70° C.
  4. temperaturethe mixture was cooled to room temperature
  5. customthe solvent was evaporated
  6. addition10% Aqueous citric acid solution (500 mL) was added to the residue
  7. extractionThe mixture was extracted with ethyl acetate (2.0 L)
  8. washsequentially washed with water (500 mL) and saturated aqueous sodium chloride solution (200 mL)
  9. dry with materialdried over magnesium sulfate
  10. filtrationAfter filtration and evaporation

Sources & evidence

ORD record
ord-e4755ddd317d41efba754e88f51471fc
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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