Water → [3-Benzyloxy-4-[2-(thiophene-2-yl)vinyl]phenyl]dibutylamine

HRID 85243

反応式

HRID 85243 の反応式
C1([Li])C=CC=CC=1.[Cl-].[C:9]1([CH2:14][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:13][CH:12]=[CH:11][CH:10]=1.[CH2:34]([O:41][C:42]1[CH:49]=[C:48]([N:50]([CH2:55][CH2:56][CH2:57][CH3:58])[CH2:51][CH2:52][CH2:53][CH3:54])[CH:47]=[CH:46][C:43]=1[CH:44]=O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.O>O1CCCC1.C(OCC)(=O)C>[CH2:34]([O:41][C:42]1[CH:49]=[C:48]([N:50]([CH2:55][CH2:56][CH2:57][CH3:58])[CH2:51][CH2:52][CH2:53][CH3:54])[CH:47]=[CH:46][C:43]=1[CH:44]=[CH:14][C:9]1[S:13][CH:12]=[CH:11][CH:10]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

参加物

7

反応物 4

HCID 962WaterHCID 115747672-Thienylmethyltriphenylphosphonium chlorideHCID 866675422-Benzyloxy-4-dibutylaminobenzaldehydeHCID 178506676HCID 178506676、化合物

生成物 1

HCID 68008929[3-Benzyloxy-4-[2-(thiophene-2-yl)vinyl]phenyl]dibutylamine収率 92.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

In a stream of argon, to 25 ml of tetrahydrofuran was added 3.3 g of phenyllithium (19% solution in dibutylether) (7.46 mmol), and 2.68 g (6.79 mmol) of 2-thenyl triphenylphosphonium chloride was added thereto under ice cooling. Next, 2.3 g (6.78 mmol) of 2-benzyloxy-4-dibutylaminobenzaldehyde was dissolved in tetrahydrofuran and added dropwise. The mixture was stirred under ice cooling for 2 hours. After the reaction mixture was poured into water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. To the residue, 40 ml of ethyl acetate/hexane (4/1) was added and the precipitate was filtered off. The filtrate was concentrated and then purified by silica gel column chromatography to give 2.64 g of a yellow oily matter (yield: 92.9%).

後処理

  1. additionwas added
  2. additionadded dropwise
  3. washwashing with a saturated saline solution
  4. dry with materialdrying over anhydrous sodium sulfate, and concentration
  5. additionTo the residue, 40 ml of ethyl acetate/hexane (4/1) was added
  6. filtrationthe precipitate was filtered off
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel column chromatography
  9. customto give 2.64 g of a yellow oily matter (yield: 92.9%)

出典と根拠

ORDレコード
ord-39765a4373ad458191737110c190b852
出典データセット
uspto-grants-2014_09
特許番号
US08846955B2

関連ノート

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