Triethylamine → (E)-tert-butyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate

HRID 632639ノート

反応式

HRID 632639 の反応式
Br[C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[C:8]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:9]=3[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:35]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])(=[O:38])[CH:36]=[CH2:37]>CN(C=O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:25][O:24][C:21]1[CH:22]=[CH:23][C:8]2[C:7]([O:6][C:5]3[CH:26]=[CH:27][C:2](/[CH:37]=[CH:36]/[C:35]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[CH:3][CH:4]=3)=[C:11]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[S:10][C:9]=2[CH:20]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 867306523-(4-Bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene

生成物 1

HCID 86730644(E)-tert-butyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate収率 63%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-(4-bromophenoxy)-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene (79 mg, 0.18 mmol) in DMF (1.7 mL) was added triethylamine (0.125 mL, 0.90 mmol) followed by tert-butyl acrylate (0.184 mL, 1.25 mmol) and Pd(PPh3)2Cl2 (18.9 mg, 0.03 mmol). The mixture was then subjected to microwave irradiation for 1 h at 120° C. after which the reaction was diluted with water (15 mL) and extracted with EtOAc (4×10 mL). The combined organic layers were washed with brine (30 mL), passed through a phase separator to remove water and concentrated in vacuo to give the crude product as an orange oil which was purified by column chromatography (SiO2, 0-50% EtOAc/Heptane) to give (E)-tert-butyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate as a pale yellow oil (55 mg, 0.11 mmol, 63% yield). 1H NMR (400 MHz, CDCl3) δ ppm=1.44 (s, 9H), 3.71 (s, 3 H), 3.78 (s, 3 H), 6.13 (d, J=15.66 Hz, 1 H), 6.76-6.83 (m, 3 H), 6.86 (m, J=8.59 Hz, 2 H), 7.14-7.19 (m, 2 H), 7.31 (m, J=8.59 Hz, 2 H), 7.42 (d, J=16.17 Hz, 1 H), 7.54 (d, J=8.59 Hz, 2 H).

後処理

  1. customirradiation for 1 h at 120° C. after which the reaction
  2. extractionextracted with EtOAc (4×10 mL)
  3. washThe combined organic layers were washed with brine (30 mL)
  4. customto remove water
  5. concentrationconcentrated in vacuo
  6. customto give the crude product as an orange oil which
  7. customwas purified by column chromatography (SiO2, 0-50% EtOAc/Heptane)

出典と根拠

ORDレコード
ord-916cbfc21f1e405fa72b6d04a5658b07
出典データセット
uspto-grants-2016_04
特許番号
US09321746B2

反応ノート

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