Dichloromethane → 3-(2,3'-Diisobutyl-4'-methoxy-biphenyl-4-yl)propionitrile

HRID 25844

反応式

HRID 25844 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]#[N:16])=[CH:9][C:8]=1[CH2:17][CH:18]([CH3:20])[CH3:19])(=O)=O.[CH2:23]([C:27]1[CH:28]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH:24]([CH3:26])[CH3:25].C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>COCCOC.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:17]([C:8]1[CH:9]=[C:10]([CH2:13][CH2:14][C:15]#[N:16])[CH:11]=[CH:12][C:7]=1[C:29]1[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:27]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH:28]=1)[CH:18]([CH3:20])[CH3:19]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 121347033-Isobutyl-4-(trifluoromethylsulfonyloxy)benzenepropanenitrileHCID 121347052-(3-Isobutyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 225652533-(2,3'-Diisobutyl-4'-methoxy-biphenyl-4-yl)propionitrile収率 100%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 20074477Dimethoxyethane ethanol溶媒

反応条件

温度
80 °C

実験手順

294.8 mg (0.88 mmol) 4-(2-Cyanoethyl)-2-isobutylphenyl-trifluormethanesulfonate (6), 312.9 mg (1.08 mmol, 1.23 eq.) 2-(3-Isobutyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (11) and 156 mg (135 μmol, 0.15 eq.) Pd(Ph3P)4 were dissolved in 20 ml DME/EtOH (9+1). To this yellow solution 0.88 ml (1.76 mmol, 2.00 eq.) of a 2 M aq. Na2CO3-solution was added and the resulting mixture was heated at 80° C. for 17 h. After concentrating the mixture in vacuo the residue was taken up in water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Column chromatography (CH2Cl2) yielded 305.9 mg (0.88 mmol, 99.45%) 3-(2,3′-Diisobutyl-4′-methoxy-biphenyl-4-yl)propionitrile (73) as a clear oil. Rf (CH2Cl2)=0.68. 1H-NMR (500 MHz, CDCl3): δ=0.67 (d, 6H, J=6.62 Hz, 2*CH3), 0.85 (d, 6H, J=6.62 Hz, 2*CH3), 1.61 (m, 1H, CH), 1.89 (m, 1H, CH), 2.44 (d, 2H, J=7.25 Hz, CH2), 2.45 (d, 2H, J=7.25 Hz, CH2), 2.59 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.91 (t, 2H, J=7.41 Hz, CH2CH2CN), 3.79 (s, 3H, OCH3), 6.80 (d, 1H, J=8.36 Hz), 6.94 (d, 1H, J=2.21 Hz), 6.98-7.04 (m, 3H), 7.09 (d, 1H, J=7.57 Hz). MS (EI): m/z=350 (23), 349 (90), 307 (10), 306 (35), 290 (39), 250 (15), 248 (17), 247 (100), 246 (24), 209 (21), 191 (16), 178 (10), 147 (10), 145 (17), 144 (19), 117 (13), 105 (25), 83 (11), 57 (18). HR-MS (EI): Calcd. for C24H31NO: 349.240564. Found: 349.240765.

後処理

  1. concentrationAfter concentrating the mixture in vacuo the residue
  2. extractionextracted with CH2Cl2
  3. dry with materialfractions were dried over MgSO4
  4. customevaporated

出典と根拠

ORDレコード
ord-d956c5d8dd904c77b91edd467b105a47
出典データセット
uspto-grants-2005_02
特許番号
US06858600B2

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