Lithium diisopropylamide → HCID 66926079, compound

HRID 2170827Notes

Reaction equation

HRID 2170827 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[C:10]([C:14]3[C:15](=[O:21])[CH2:16][CH2:17][C:18]=3[O:19][CH3:20])[CH:9]=2)=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].I[CH2:31][CH:32]1[CH2:36][CH2:35][O:34][CH2:33]1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[C:10]([C:14]3[C:15](=[O:21])[CH:16]([CH2:31][CH:32]4[CH2:36][CH2:35][O:34][CH2:33]4)[CH2:17][C:18]=3[O:19][CH3:20])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 27630063-(Iodomethyl)oxolaneHCID 66926146HCID 66926146, compound

Product 1

HCID 66926079HCID 66926079, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-3-methoxy-cyclopent-2-enone (285 mg, 0.89 mmol) in anhydrous tetrahydrofuran (6 ml) at −78° C. under an atmosphere of nitrogen is added lithium diisopropylamide (1.8M in THF/heptanes/ethylbenzene; 0.55 ml, 1.0 mmol) dropwise over a period of 5 minutes and the reaction allowed to stir at −78° C. for 30 minutes. A solution of 3-iodomethyl tetrahydrofuran (212 mg, 1 mmol) in anhydrous tetrahydrofuran (1 ml) was then added dropwise over a period of 5 minutes before the reaction was allowed to warm to room temperature and stirred for a further 30 minutes. The reaction was quenched by the addition of saturated aqueous ammonium chloride solution (50 ml) and extracted with ethyl acetate (50 ml) and the organic later separated, dry loaded onto silica and purified by flash chromatography to give 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-3-methoxy-5-(tetrahydro-furan-3-ylmethyl)-cyclopent-2-enone (150 mg)

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for a further 30 minutes
  3. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride solution (50 ml)
  4. extractionextracted with ethyl acetate (50 ml)
  5. customthe organic later separated
  6. customdry loaded onto silica
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-af46ed40af624f33b4b56ca2b2f52752
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

Loading…