HCID 86714050, compound → HCID 86714049, compound
Reaction equation
[CH2:1]([C:3]1[CH:60]=[CH:59][C:6]([CH2:7][C:8]2[C:9]([Cl:58])=[C:10]([O:54][CH2:55][CH2:56]Cl)[C:11](Br)=[C:12]([CH:14]3[C@H:19]([O:20]CC4C=CC=CC=4)[C@@H:18]([O:28][CH2:29]C4C=CC=CC=4)[C@H:17]([O:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C@@H:16]([CH2:44][O:45][CH2:46]C4C=CC=CC=4)[O:15]3)[CH:13]=2)=[CH:5][CH:4]=1)[CH3:2].[CH2:61]([Li])[CH2:62][CH2:63][CH3:64]>C1COCC1>[CH2:61]([O:20][C@@H:19]1[C@@H:18]([O:28][CH2:29][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C@H:17]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@@H:16]([CH2:44][O:45][CH2:46][C:60]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:59]=2)[O:15][CH:14]1[C:12]1[C:11]2[CH2:56][CH2:55][O:54][C:10]=2[C:9]([Cl:58])=[C:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:60][CH:59]=2)[CH:13]=1)[C:62]1[CH:17]=[CH:16][CH:44]=[CH:64][CH:63]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of compound 71 (1.16 g, 1.27 mmol) in THF (12.7 mL) was added dropwise n-butyllithium (2.5 M in hexane, 1.27 mL, 3.17 mmol) at −78° C. under an atmosphere of nitrogen. The mixture was stirred for 18 hours at −78° C. to 5° C. The mixture was quenched with 1 N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 72 (493 mg, 48%) as brown oil.
Workup
- customThe mixture was quenched with 1 N HCl
- extractionextracted with EtOAc
- washThe organic layer was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-e77e0e2de2d5483485c8610ba0f68d14
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09371303B2
Reaction notes
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