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

HRID 2420646노트

반응식

HRID 2420646 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-63485a51519049168b72d9ac649dbebd
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07955664B2

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