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Lithium hexamethyldisilazane → 2-(4-Bromo-2,6-dimethylphenyl)-5-[hydroxy(tetrahydropyran-4-yl)methyl]-3-methoxycyclopent-2-enone

HRID 514200
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HRID 514200 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:16])[CH2:11][CH2:12][C:13]=2[O:14][CH3:15])=[C:4]([CH3:17])[CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:28]1[CH:33]([CH:34]=[O:35])[CH2:32][CH2:31][O:30][CH2:29]1>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:17])[C:5]([C:9]2[C:10](=[O:16])[CH:11]([CH:34]([OH:35])[CH:33]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[CH2:12][C:13]=2[O:14][CH3:15])=[C:6]([CH3:8])[CH:7]=1
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참가 물질

5

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HCID 2733832Lithium hexamethyldisilazaneHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 668681542-(4-Bromo-2,6-dimethylphenyl)-3-methoxy-cyclopent-2-enone

생성물 1

HCID 896013392-(4-Bromo-2,6-dimethylphenyl)-5-[hydroxy(tetrahydropyran-4-yl)methyl]-3-methoxycyclopent-2-enone

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-75 °C

실험 절차

To a solution of 2-(4-bromo-2,6-dimethylphenyl)-3-methoxycyclopent-2-enone (7.5 g, 26.0 mmol) in anhydrous tetrahydrofuran (70 ml) under a nitrogen atmosphere is added lithium bis(trimethylsilyl)amide (44.6 ml, 31.0 mmol, 0.7M in tetrahydrofuran) dropwise at −75°C. After stirring for 40 minutes at this temperature a second solution of tetrahydropyranyl-4-carboxaldehyde (5.90 g, 52.0 mmol) in tetrahydrofuran (70 ml) is added over 20 minutes, and the resulting solution is stirred at −75°C. for 2 hours. After warming to room temperature the mixture is stirred for a further 2 hours, then is quenched with ice cold water (100 ml) and extracted with ethyl acetate (3×150 ml). Organics are combined, dried over sodium sulphate, filtered and the filtrate is concentrated in vacuo to afford 2-(4-bromo-2,6-dimethylphenyl)-5-[hydroxy(tetrahydropyran-4-yl)methyl]-3-methoxycyclopent-2-enone. This material is used directly in the next step without further purification.

후처리

  1. additionis added over 20 minutes
  2. temperatureAfter warming to room temperature the mixture
  3. stirringis stirred for a further 2 hours
  4. customis quenched with ice cold water (100 ml)
  5. extractionextracted with ethyl acetate (3×150 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated in vacuo

출처 및 근거

ORD 기록
ord-1485ee43c98d429bb6d928d729131d75
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09107415B2

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