Hydrochloric Acid → HCID 9855945, compound

HRID 967762Notes

Reaction equation

HRID 967762 reaction equation
C([Li])CCC.[CH2:6]([CH:10]([CH2:14]C)[C:11]([OH:13])=[O:12])C(C)C.[CH:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1)([CH3:18])[CH3:17].Cl>O1CCCC1.C(NC(C)C)(C)C>[CH:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][C:10]([CH3:14])([CH3:6])[C:11]([OH:13])=[O:12])=[CH:21][CH:20]=1)([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 749164-Isopropylbenzyl chlorideHCID 164536Pentanoic acid, 2-​ethyl-​4-​methyl-HCID 178418339Butyllithium

Product 1

HCID 9855945HCID 9855945, compound

Reagents, catalysts & solvents 2

HCID 7912DiisopropylamineSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

in tetrahydrofuran (40 ml) was dissolved in diisopropylamine (3.08 ml) and to the mixture was added n-butyl lithium (13.8 ml; 1.6 M hexane solution) at −78° C. and thereto was added isobutylbutyric acid (0.93 ml) dropwise and the mixture was stirred for 1 hour at 30° C. To the reaction mixture was added a solution of 4-isopropylbenzyl chloride (2.19 g) in tetrahydrofuran (10 ml) at −78° C. and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured to cool hydrochloric acid and was extracted with ethyl acetate. The extract was concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1) to give the title compound (1.73 g) having the following physical data.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. additionThe reaction mixture was poured
  3. extractionwas extracted with ethyl acetate
  4. concentrationThe extract was concentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-870900bfb49943ad8c35dad46e3bce62
Source dataset
uspto-grants-2005_10
Patent number
US06956033B2

Reaction notes

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