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Lithium diisopropylamide → ethyl (E)-3-(3-n-propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-fluoropent-2-enoate

HRID 1744912
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HRID 1744912 반응식
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[F:7])=[O:5].C([N-]C(C)C)(C)C.[Li+].[CH2:24]([O:27][C:28]1[C:29]([C:42](=O)[CH2:43][CH3:44])=[CH:30][C:31]2[C:32]([CH3:41])([CH3:40])[CH2:33][CH2:34][C:35]([CH3:39])([CH3:38])[C:36]=2[CH:37]=1)[CH2:25][CH3:26]>C1COCC1>[CH2:24]([O:27][C:28]1[C:29](/[C:42](/[CH2:43][CH3:44])=[C:6](/[F:7])\[C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:30][C:31]2[C:32]([CH3:41])([CH3:40])[CH2:33][CH2:34][C:35]([CH3:39])([CH3:38])[C:36]=2[CH:37]=1)[CH2:25][CH3:26]
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참가 물질

5

반응물 3

HCID 2724682Lithium diisopropylamideHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 22226103HCID 22226103, 화합물2회

생성물 1

HCID 86593752ethyl (E)-3-(3-n-propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2-fluoropent-2-enoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

Triethyl 2-fluoro-2-phosphonoacetate (5.72 mL, 28.1 mmol, was added to a stirring solution of lithium diisopropylamide (28.1 mmol) in THF (54 mL) at −78° C. under argon. The dry ice bath was removed for about ten minutes, and then the solution was cooled again to −78° C. A solution of 1-(3-n-propoxy5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)propan-1-one (Intermediate 7, 2.70 g, 9.36 mmol) and THF. (10 mL) was added, and the solution was stirred at 0° C. for 2 h. The reaction was quenched at −78° C. by adding saturated ammonium chloride. The solution was warmed to room temperature and the products were extracted three times with ether. The combined organic layers were washed with water, brine and dried over magnesium sulfate. The solvent was removed in vacuo to give the title compound.

후처리

  1. customThe dry ice bath was removed for about ten minutes
  2. addition(10 mL) was added
  3. customThe reaction was quenched at −78° C.
  4. additionby adding saturated ammonium chloride
  5. temperatureThe solution was warmed to room temperature
  6. extractionthe products were extracted three times with ether
  7. washThe combined organic layers were washed with water, brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-a6917a40fd254206a8bde9b2a862d313
출처 데이터셋
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07019034B2

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