Water → (E)-3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylic acid

HRID 632645ノート

反応式

HRID 632645 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([O:22]C)=[O:21])=[CH:14][CH:13]=3)=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[S:8][C:7]=2[CH:32]=1.C1COCC1.O.[Li+].[OH-]>C(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([O:11][C:12]3[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20]([OH:22])=[O:21])=[CH:14][CH:13]=3)=[C:9]([C:24]3[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=3)[S:8][C:7]=2[CH:32]=1

参加物

7

反応物 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86730659(E)-methyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate

生成物 1

HCID 86730661(E)-3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylic acid収率 92%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

To a 30 mL vial containing (E)-methyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate (110 mg, 0.25 mmol) was added THF (2.00 mL), MeOH (1.00 mL). H2O (1.00 mL) and LiOH (29.5 mg, 1.23 mmol). The resulting mixture was stirred at room temperature for 60 min after which the reaction was concentrated in vacuo, diluted with water, and acidified to pH 2 with 6 M HCl causing a precipitate to form. The mixture was diluted with 20 mL DCM and 2 mL MeOH and the organic layer was collected (phase separator) and concentrated in vacuo to afford (E)-3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylic acid (98 mg, 0.23 mmol, 92% yield) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ ppm=7.51-7.69 (m, 5 H), 7.43 (d, J=2.02 Hz, 1H), 7.25 (d, J=9.09 Hz, 1 H), 6.88-7.02 (m, 5 H), 6.37 (d, J=15.66 Hz, 1 H), 3.89 (s, 3 H), 3.80 (s, 3 H), LC/MS (m/z, MH+): 433.0.

後処理

  1. concentrationwas concentrated in vacuo
  2. additiondiluted with water
  3. customto form
  4. customthe organic layer was collected (phase separator)
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5d6f0f52734c4fed8968fa7254cd73fb
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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