Potassium Carbonate → E-4-[5-[2-(4-tert-Butylbenzyloxy)phenyl]-3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)pent-4-enyl]benzonitrile

HRID 1921896노트

반응식

HRID 1921896 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([F:40])[C:28]=1[O:29][Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[CH2:5][CH:6](/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25])[CH2:7][CH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[C:47]([C:51]1[CH:58]=[CH:57][C:54]([CH2:55]Br)=[CH:53][CH:52]=1)([CH3:50])([CH3:49])[CH3:48]>C(#N)C.C(OCC)(=O)C>[C:47]([C:51]1[CH:52]=[CH:53][C:54]([CH2:55][O:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2/[CH:18]=[CH:17]/[CH:6]([CH2:5][C:4]2[CH:26]=[C:27]([F:40])[C:28]([O:29][Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:32])[CH3:33])=[C:2]([F:1])[CH:3]=2)[CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=2)=[CH:57][CH:58]=1)([CH3:50])([CH3:48])[CH3:49]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 579719094-[(4E)-3-{3,5-difluoro-4-[(triisopropylsilyl)oxy]benzyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzonitrile

생성물 1

HCID 57971908E-4-[5-[2-(4-tert-Butylbenzyloxy)phenyl]-3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)pent-4-enyl]benzonitrile

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

1.7 g (3 mmol) of 4-[(4E)-3-{3,5-difluoro-4-[(triisopropylsilyl)oxy]benzyl}-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzonitrile in 35 ml of acetonitrile are mixed with 627 mg (4.5 mmol) of potassium carbonate and 1 g (4.5 mmol) of 4-tert-butylbenzyl bromide and stirred under reflux for 12 hours. The solvent is stripped off in vacuo, and the residue is taken up in ethyl acetate. The organic phase is washed once with sodium bicarbonate solution and once with sodium chloride solution, dried over sodium sulfate and concentrated. The crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 628 mg (85% purity, 0.76 mmol, 25% of theory) of the title compound are obtained.

후처리

  1. temperatureunder reflux for 12 hours
  2. washThe organic phase is washed once with sodium bicarbonate solution and once with sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)

출처 및 근거

ORD 기록
ord-a3c43b95ea1746b9b2e647c22ef85fd2
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173704B2

반응 노트

불러오는 중…