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

HRID 1921896ノート

反応式

HRID 1921896 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a3c43b95ea1746b9b2e647c22ef85fd2
出典データセット
uspto-grants-2012_05
特許番号
US08173704B2

反応ノート

読み込み中…