Hydrochloric Acid → 6-Fluoro-3-pentylchroman-7-carbaldehyde

HRID 2420646ノート

反応式

HRID 2420646 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:8][O:9]2)=[CH:4][C:3]=1[F:17].C([Li])CCC.[CH:23](N1CCCCC1)=[O:24].Cl>C1COCC1.CCCCCC.O>[F:17][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[CH:23]=[O:24])[O:9][CH2:8][CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:6]2

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 174291-PiperidinecarboxaldehydeHCID 592883377-Bromo-6-fluoro-3-pentylchromanHCID 178418339Butyllithium

生成物 1

HCID 592883516-Fluoro-3-pentylchroman-7-carbaldehyde

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

15.5 g (51.5 mmol) of 7-bromo-6-fluoro-3-pentylchroman are dissolved in 85 ml of THF, and 35 ml (55.7 mmol) of a 15 percent solution of n-butyllithium in n-hexane are slowly added at −70° C. After 1 h, 6.3 ml (56.7 mmol) of N-formylpiperidine in 15 ml of THF are added dropwise, and the mixture is stirred for 1 h. The batch is subsequently allowed to thaw, added to water, acidified using dil. hydrochloric acid and extracted three times with MTB ether. The combined org. phases are washed with water and sat. sodium chloride soln. and dried over sodium sulfate, the solvent is removed in vacuo, and the residue is recrystallised from heptane at −25° C., giving 6-fluoro-3-pentylchroman-7-carbaldehyde as colourless crystals (Rf=0.4; 1-chlorobutane).

後処理

  1. extractionextracted three times with MTB ether
  2. washphases are washed with water and sat. sodium chloride soln
  3. dry with materialand dried over sodium sulfate
  4. customthe solvent is removed in vacuo
  5. customthe residue is recrystallised from heptane at −25° C.

出典と根拠

ORDレコード
ord-63485a51519049168b72d9ac649dbebd
出典データセット
uspto-grants-2011_06
特許番号
US07955664B2

反応ノート

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