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Hydrochloric Acid → [1-Bromo-6-(3-phenylacetyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid

HRID 1373871
ノート
印刷プレビュー

反応式

HRID 1373871 の反応式
C([O:3][C:4](=[O:36])[CH2:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[C:18]=3[C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:13]=2)[C:8]=1[Br:35])C.[OH-].[K+].Cl>C1COCC1.O>[Br:35][C:8]1[C:9]2[C:14](=[CH:13][C:12]([C:17]3[S:21][C:20]4[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=4[C:18]=3[C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[O:6][CH2:5][C:4]([OH:36])=[O:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69410855[1-Bromo-6-(3-phenylacetyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester

生成物 1

HCID 11237897[1-Bromo-6-(3-phenylacetyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid収率 24.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回
HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of [1-bromo-6-(3-phenylacetyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester (0.427 g, 0.764 mmol) and potassium hydroxide (0.162 g 2.89 mmol) in THF (125 mL) and water (125 mL) was stirred at ambient temperature for two hours. It was then poured in excess water and acidified with 2N hydrochloric acid. This was then extracted with ethyl acetate and washed with water and brine. The organic phase was dried with anhydrous magnesium sulfate, filtered, solvent evaporated and purified by HPLC using 65% acetonitrile (0.1% trifluoroacetic acid) in water as the mobile phase. Evaporating the solvent and extracting with ethyl acetate, washing with water and brine, drying with anhydrous magnesium sulfate, filtering, concentrating and drying in vacuo at 60° C. for 25 minutes to yield [1-bromo-6-(3-phenylacetyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid as a yellow solid (0.100 g, 24.6%): MP: 170–2° C.; mass spectrum (+EI, [M+H]+) m/z 531/533. 1H NMR (500 MHz, DMSO-d6): δ13.0–13.3 (br, 1H), 8.27 (d, 1H, J=8.86 Hz), 8.16 (d, 1H, J=1.52 Hz), 8.06–8.12 (m, 2H), 7.89–7.92 (m, 1H), 7.81 (dd, 1H, J=8.86 Hz and 1.83 Hz), 7.44–7.52 (m, 3H), 7.13–7.19 (m, 3H), 6.92–6.94 (m, 2H), 5.02 (s, 2H), 3.81 ppm (s, 2H).

後処理

  1. extractionThis was then extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customsolvent evaporated
  6. custompurified by HPLC
  7. customEvaporating the solvent
  8. extractionextracting with ethyl acetate
  9. washwashing with water and brine
  10. dry with materialdrying with anhydrous magnesium sulfate
  11. filtrationfiltering
  12. concentrationconcentrating
  13. customdrying in vacuo at 60° C. for 25 minutes

出典と根拠

ORDレコード
ord-c667beb5a41d421e9000710fe2eee57f
出典データセット
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07163954B2

反応ノート

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