Propylethinylcarbinol → 6-(1-Ethynylbutoxy)-7,8-difluoro-2-pentylchroman

HRID 1873313노트

반응식

HRID 1873313 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)=[CH:4][C:3]=1[OH:18].[CH:19]#[C:20][CH:21](O)[CH2:22][CH2:23][CH3:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.O>[C:20]([CH:21]([O:18][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([F:12])[C:2]=1[F:1])[O:9][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:7][CH2:6]2)[CH2:22][CH2:23][CH3:24])#[CH:19]

참가 물질

7

반응물 4

HCID 7746PropylethinylcarbinolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 46834772HCID 46834772, 화합물

생성물 1

HCID 581519006-(1-Ethynylbutoxy)-7,8-difluoro-2-pentylchroman

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

10.0 g (39.0 mmol) of 7,8-difluoro-2-pentylchroman-6-ol are initially introduced in 140 ml of THF together with 4.0 g (41.0 mmol) of 1-hexyn-3-ol and 11.3 g (42.9 mmol) of triphenylphosphine, and 9.1 ml (46.8 mmol) of DIAD are added over the course of 20 min with ice-cooling. After 18 h at RT, water is added, and the mixture is extracted a number of times with MTBE. The combined organic phases are washed with water and saturated sodium chloride soln., and the solution is dried using sodium sulfate. The residue remaining after removal of the solvents is purified by column chromatography (SiO2, n-heptane:MTBE=2:1), giving 6-(1-ethynylbutoxy)-7,8-difluoro-2-pentylchroman as a yellow oil.

후처리

  1. additionare added over the course of 20 min with ice-
  2. temperaturecooling
  3. extractionthe mixture is extracted a number of times with MTBE
  4. washThe combined organic phases are washed with water and saturated sodium chloride soln
  5. custom, and the solution is dried
  6. customafter removal of the solvents
  7. customis purified by column chromatography (SiO2, n-heptane:MTBE=2:1)

출처 및 근거

ORD 기록
ord-2fd8d632df444939aeb159f484faf82f
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08303844B2

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