Dimethylformamide → HCID 74325984, compound
Reaction equation
[CH2:1]([S:11]([CH2:14]/[CH:15]=[C:16](/[CH2:18][CH2:19][CH:20]=C(C)C)\C)(=[O:13])=[O:12])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].CC([O-:28])(C)C.[K+].[CH2:30](Br)/[CH:31]=[C:32](/[CH2:34][CH2:35][CH:36]=[C:37]([CH3:39])C)\[CH3:33].CN([CH:44]=[O:45])C>>[C:14]1([S:11]([CH:1]([CH2:30][CH:31]=[C:32]([CH3:33])[CH2:34][CH2:35][CH:36]=[C:37]([CH3:39])[CH:44]=[O:45])[CH:2]=[C:3]([CH3:4])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH:10]=[O:28])(=[O:12])=[O:13])[CH:15]=[CH:16][CH:18]=[CH:19][CH:20]=1Participants
5
Procedure
To a stirred solution of geranyl sulfone (I) (5.00 g 17.93 mmol) in DMF (50 mL) at −20° C. was added t-BuOK (2.33 g, 19.72 mmol). The resulting orange mixture was stirred at that temperature for 30 min, and a solution of geranyl bromide (4.28 g, 19.72 mmol) in DMF (10 mL) was added. The mixture was stirred at −20° C. for 1 h, and quenched with 1 M HCl solution (20 mL). The mixture was extracted with EtOAc (50 mL), washed with 1 M HCl (10 mL×3), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give the coupling product (J) (7.10 g, 17.12 mmol) in 95% yield.
Workup
- stirringThe mixture was stirred at −20° C. for 1 h
- customquenched with 1 M HCl solution (20 mL)
- extractionThe mixture was extracted with EtOAc (50 mL)
- washwashed with 1 M HCl (10 mL×3)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-a662b5d4abe8420bbdc052007583a8d1
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158838B2
Reaction notes
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