Hydrochloric Acid → HCID 9855945, compound
Reaction equation
C(N[CH:5]([CH3:7])[CH3:6])(C)C.C([Li])CCC.C([O:17][C:18](=[O:20])C)C(C)C.[CH:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1)([CH3:23])[CH3:22].Cl>O1CCCC1>[CH:21]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28][C:5]([CH3:6])([CH3:7])[C:18]([OH:20])=[O:17])=[CH:26][CH:25]=1)([CH3:23])[CH3:22]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
Diisopropylamine (3.08 ml) was dissolved in tetrahydrofuran (40 ml) and to the mixture was added n-butyl lithium (13.8 ml; 1.6M in hexane) at −78° C. and then was added isobutylacetate (0.93 ml) 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 for 2 hours at room temperature. The reaction mixture was poured into cool hydrochloric acid and the mixture 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
- stirringthe mixture was stirred for 2 hours at room temperature
- additionThe reaction mixture was poured
- extractionthe mixture was extracted with ethyl acetate
- concentrationThe extract was concentrated
- customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1)
Sources & evidence
- ORD record
- ord-678092de82fe40678ce2d3b3336063f5
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07378428B2
Reaction notes
Loading…