Water → HCID 22903415, compound
Reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[CH2:9][N:10]([C:11]([O:13]C(C)(C)C)=[O:12])[C:4]=2[CH:3]=1.[Li][CH2:25][CH2:26][CH2:27][CH3:28].[OH2:29]>C1COCC1>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]2[O:6][C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[CH:9]3[CH:28]([C:27]4[CH:23]=[CH:2][C:3]([CH2:4][C:5]([OH:6])=[O:29])=[CH:25][CH:26]=4)[O:13][C:11](=[O:12])[N:10]3[C:4]=2[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A stirring solution of 1 (2.0 g, 6.04 mmol) in 40 mL of THF was cooled to -78° C. followed by the addition of n-BuLi (1.6M, 4.32 mL, 6.91 mmol). The mixture was stirred at -78° C. for 30 minutes and treated with methyl 4-formyl benzoate (1.2 g, 7 mmol), and then slowly warmed to room temperature and let stir for 1.5 hours at room temperature, and then diluted with 16 mL of water. The mixture was then extracted with ethyl acetate (200 mL×2) and the combined extracts were washed with brine (saturated, 200 mL) and dried (Na2SO4). The extracts were concentrated to give the crude product (2.95 g), which was purified by medium pressure chromatography with 1:4 EtOAc:Hexane, to yield 16 and 17 as follows:
Workup
- temperatureslowly warmed to room temperature
- stirringlet stir for 1.5 hours at room temperature
- extractionThe mixture was then extracted with ethyl acetate (200 mL×2)
- washthe combined extracts were washed with brine (saturated, 200 mL)
- dry with materialdried (Na2SO4)
- concentrationThe extracts were concentrated
- customto give the crude product (2.95 g), which
- customwas purified by medium pressure chromatography with 1:4 EtOAc
Sources & evidence
- ORD record
- ord-b7dd42d778c84706a9c419e629016440
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05488046
Reaction notes
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