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Potassium Phosphate, Tribasic → [4'-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-3-chloro-2'-methyl-biphenyl-4-yl]-acetic Acid Methyl Ester

HRID 546915
ノート
印刷プレビュー

反応式

HRID 546915 の反応式
[C:1]([Si:5]([O:8][CH:9]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH2:41][CH3:42])([C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[C:27]([CH3:40])[CH:26]=2)[CH2:23][CH3:24])=[CH:18][C:17]=1[CH3:43])[C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:81][O:82][C:83](=[O:93])[CH2:84][C:85]1[CH:90]=[CH:89][C:88](Cl)=[CH:87][C:86]=1[Cl:92]>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:81][O:82][C:83](=[O:93])[CH2:84][C:85]1[CH:90]=[CH:89][C:88]([C:28]2[CH:29]=[CH:30][C:25]([C:22]([C:19]3[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][CH:9]([O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:6])[CH3:7])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:17]([CH3:43])[CH:18]=3)([CH2:23][CH3:24])[CH2:41][CH3:42])=[CH:26][C:27]=2[CH3:40])=[CH:87][C:86]=1[Cl:92]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 2734106Methyl 2,4-dichlorobenzeneacetateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 577089262-[4-(1-{4-[3-(t-Butyldimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

生成物 1

HCID 57709101
[4'-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-3-chloro-2'-methyl-biphenyl-4-yl]-acetic Acid Methyl Ester
収率 17.5%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

Degassed toluene (0.13 mL) and water (0.013 mL) were added to t-butyl-(1-{2-[4-(1-ethyl-1-{4-[4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-ethyl}-2,2-dimethyl-propoxy)dimethylsilane (Example 23-(1); 15.7 mg, 0.0259 mmol), palladium (II) acetate (0.8 mg, 0.004 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (3 mg, 0.007 mmol) and potassium phosphate (20.0 mg, 0.0942 mmol). After replacement with nitrogen, (2,4-dichloro-phenyl)acetic acid methyl ester (Example 41; 17 mg, 0.078 mmol) was added. After replacement with nitrogen, the mixture was heated while stirring at an external temperature of 96 to 104° C. for 30 minutes. The reaction mixture was diluted with diethyl ether and filtered through cotton plug, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=50/1) to give the title compound (3 mg, 17%).

後処理

  1. customDegassed toluene (0.13 mL) and water (0.013 mL)
  2. temperatureAfter replacement with nitrogen, the mixture was heated
  3. filtrationfiltered through cotton plug
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=50/1)

出典と根拠

ORDレコード
ord-7463ae4f34b94a578c4127c0da4f4c2e
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07935688B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート