Lithium diisopropylamide → HCID 46928345, 화합물

HRID 336083노트

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HRID 336083 반응식
[CH3:1][O:2][C:3]1[CH2:7][CH2:6][C:5](=[O:8])[C:4]=1[C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17].C([N-]C(C)C)(C)C.[Li+].Cl[CH2:27][C:28]1[CH:32]=[C:31]([CH3:33])[O:30][N:29]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH2:7][CH:6]([CH2:27][C:28]2[CH:32]=[C:31]([CH3:33])[O:30][N:29]=2)[C:5](=[O:8])[C:4]=1[C:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17]

참가 물질

5

반응물 3

HCID 2724682Lithium diisopropylamideHCID 27357633-(Chloromethyl)-5-methyl-1,2-oxazoleHCID 155776462-(2,4,6-Trimethylphenyl)-3-methoxy-cyclopent-2-enone

생성물 1

HCID 46928345HCID 46928345, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

A flask is charged with 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (230 mg, 1 mmol), purged with nitrogen and anhydrous THF (5 ml) added. The resulting solution is cooled to −78° C. and lithium diisopropylamide (1.8M solution in hexane/THF/ethyl benzene) (0.61 ml, 1.1 mmol) is added dropwise and the reaction stirred at −78° C. for a further 30 minutes. A solution of 3-chloromethyl-5-methyl isoxazole in THF (1 ml) is then added in one portion, and the reaction is allowed to warm to ambient temperature and stirred for a further 2 hours. The reaction is quenched by the addition of saturated ammonium chloride solution (20 ml), and extracted with ethyl acetate (2×20 ml). The combined organics are evaporated under reduced pressure and the residue is purified by flash chromatography to give 3-methoxy-5-(5-methyl-isoxazol-3-ylmethyl)-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (132 mg)

후처리

  1. custompurged with nitrogen and anhydrous THF (5 ml)
  2. additionadded
  3. temperatureto warm to ambient temperature
  4. stirringstirred for a further 2 hours
  5. customThe reaction is quenched by the addition of saturated ammonium chloride solution (20 ml)
  6. extractionextracted with ethyl acetate (2×20 ml)
  7. customThe combined organics are evaporated under reduced pressure
  8. customthe residue is purified by flash chromatography

출처 및 근거

ORD 기록
ord-2c49d2b7eeee46a687bd806371c503d2
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889595B2

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