HCID 17837608, compound → HCID 53825396, compound

HRID 1755783Notes

Reaction equation

[Li]CCCC.[Br-].[F:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[F:18])[N:14]=[C:13]([CH2:19][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH:12]=[CH:11]2.[Br:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH2:46][CH2:47][C@@H:48]([S:57][CH2:58][C:59]1([CH2:62][C:63]([O:65][CH3:66])=[O:64])[CH2:61][CH2:60]1)[C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH:55]=O)[CH:50]=1>CCCCCC.C1COCC1>[Br:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[CH2:46][CH2:47][C@@H:48]([S:57][CH2:58][C:59]1([CH2:62][C:63]([O:65][CH3:66])=[O:64])[CH2:60][CH2:61]1)[C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH:55]=[CH:19][C:13]2[CH:12]=[CH:11][C:10]3[C:15](=[CH:16][C:17]([F:18])=[C:8]([F:7])[CH:9]=3)[N:14]=2)[CH:50]=1

Participants

Conditions

Temperature: -10 °C

Procedure

At -78° C., 1.6M BuLi in hexane (700 μL) was added to a suspension of the phosphonium salt of Step 9 (646 mg, 1.1 equiv.) in 6 mL of anh. THF and the mixture was stirred at -10° C. for 10 min. At -78° C., a solution of the aldehyde of Step 8 (515 mg, 1.12 mmol) in 4 mL of THF was then added dropwise. The mixture was stirred at -78° C. for 30 min. and at -10° C. for 30 min. and was quenched with 25% aq. NH4OAc. The product was extracted in EtOAc, dried over Na2SO4, is and purified by flash chromotography on silica with EtOAc:toluene 2.5:97.5 and 5:95.

Workup

stirringThe mixture was stirred at -78° C. for 30 min. and at -10° C. for 30 min.
customwas quenched with 25% aq. NH4OAc
extractionThe product was extracted in EtOAc
dry with materialdried over Na2SO4
custompurified by flash chromotography on silica with EtOAc:toluene 2.5:97.5 and 5:95

Sources & evidence

ORD record: ord-200086c0736e473d87180fe2d72e5cae
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438141

Reaction notes

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