N,N,N',N'-Tetramethylethylenediamine → 4,5-difluoro-7-pentyl-2-(4-propylcyclohexyl)-8,9-dihydro-7H-furo[3,2-f]chromene

HRID 2244843노트

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HRID 2244843 반응식
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[C:4]([C:18]#[C:19][CH:20]2[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][CH3:28])[CH2:22][CH2:21]2)[C:3]=1[OH:29].CN(CCN(C)C)C.C([Zn]CC)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[C:4]2[CH:18]=[C:19]([CH:20]3[CH2:21][CH2:22][CH:23]([CH2:26][CH2:27][CH3:28])[CH2:24][CH2:25]3)[O:29][C:3]=12

참가 물질

6

반응물 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 592152687,8-Difluoro-2-pentyl-5-(4-propylcyclohexylethynyl)chroman-6-olHCID 178418750HCID 178418750, 화합물

생성물 1

HCID 592152444,5-difluoro-7-pentyl-2-(4-propylcyclohexyl)-8,9-dihydro-7H-furo[3,2-f]chromene

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

3.00 g (7.41 mmol) of 7,8-difluoro-2-pentyl-5-(4-propylcyclohexylethynyl)chroman-6-ol are initially introduced together with 0.11 ml (0.74 mmol) of TMEDA, and 4.1 ml (4.1 mmol) of diethylzinc (1 M soln. in heptane) are added to the mixture at 3° C. When the evolution of gas has subsided, 11 ml of toluene are added, and the batch is refluxed for 40 h. The solution is added to sat. ammonium chloride soln., and the mixture is extracted with toluene. The combined organic phases are washed with water and sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, 1-chlorobutane:pentane=2:1). Further purification is carried out by repeated recrystallisation from ethanol at reduced temperature, giving 4,5-difluoro-7-pentyl-2-(4-propylcyclohexyl)-8,9-dihydro-7H-furo[3,2-f]chromene as a colourless solid having the phase sequence C 56° C. N 62° C. I (Δ∈=−6.8).

후처리

  1. additionare added to the mixture at 3° C
  2. temperaturethe batch is refluxed for 40 h
  3. extraction, and the mixture is extracted with toluene
  4. washThe combined organic phases are washed with water and sat. sodium chloride soln
  5. customand dried
  6. concentrationThe solution is concentrated to dryness
  7. customthe residue is purified by column chromatography (SiO2, 1-chlorobutane:pentane=2:1)
  8. customFurther purification
  9. customrecrystallisation from ethanol at reduced temperature

출처 및 근거

ORD 기록
ord-e7d2575ccf864a5fbe1d233b792a2aba
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07678929B2

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