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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
ノート
印刷プレビュー

反応式

HRID 1744912 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 2724682Lithium diisopropylamideHCID 2734865Triethyl 2-fluoro-2-phosphonoacetateHCID 22226103HCID 22226103、化合物2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a6917a40fd254206a8bde9b2a862d313
出典データセット
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07019034B2

反応ノート

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