HCID 86700761, compound → HCID 86700760, compound

HRID 2272551Notes

Reaction equation

[CH2:1]([Li])CCC.[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([CH:25]=O)=[CH:10][N:11]2[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([CH:25]=[CH2:1])=[CH:10][N:11]2[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyltriphenylphosphonium bromide (1.14 g) was suspended in tetrahydrofuran (6.0 mL), and to this solution was added n-butyl lithium (in 2.64 M hexane solution of 1.16 mL) at −78° C. The mixture was stirred at 0° C. for 1 hour and then a solution of compound (48a) (0.91 g) in tetrahydrofuran (2.0 mL) was added thereto, followed by stirring at room temperature for 1 hour. The reaction solution was partitioned with ethyl acetate and water, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed by evaporation. The residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate) to obtain compound (48b) (0.864 g, 95%) as a colorless oily substance.

Workup

stirringby stirring at room temperature for 1 hour
customThe reaction solution was partitioned with ethyl acetate and water
washthe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was removed by evaporation
customThe residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-c544f704739c4b6dbd33c74f2813df1d
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120780B2

Reaction notes

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