Hydrochloric Acid → HCID 11454785、化合物

HRID 1373867ノート

反応式

HRID 1373867 の反応式
C([O:3][C:4](=[O:33])[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:31])[CH2:27][CH2:28][CH2:29][CH3:30])[CH:13]=2)[C:8]=1[Br:32])C.[OH-].[K+].Cl>C1COCC1.O>[Br:32][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:31])[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[O:6][CH2:5][C:4]([OH:33])=[O:3]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69411771[1-Bromo-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester

生成物 1

HCID 11454785HCID 11454785、化合物収率 75.2%

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-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid ethyl ester (0.0932 g, 0.177 mmol) and potassium hydroxide (0.063 gm 1.1 mmol) in THF (5 mL) and water (5 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 dried in vacuo at 64° C. for 25 hours to yield [1-bromo-6-(3-pentanoyl-benzo[b]thiophen-2-yl)-naphthalen-2-yloxy]-acetic acid as a light yellow solid (0.0662 g, 75.2%): MP: 164–5° C.; mass spectrum (+EI, [M+H]+) m/z 497/499. 1H NMR (500 MHz, DMSO-d6): δ13.0–13.2 (br, 1H), 8.24 (d, 1H, J=8.70 Hz), 8.07–8.13 (m, 3H), 7.95–7.97 (m, 1H), 7.76 (dd, 1H, J=8.78 Hz and 1.91 Hz), 7.45–7.51 (m, 3H), 5.02 (s, 2H), 2.42 (t, 2H, J=7.22 Hz), 1.40–1.46 (m, 2H), 0.97–1.04 (m, 2H), 0.58 ppm (t, 3H, J=7.41 Hz). Elemental Analysis for C25H21BrO4S: Calcd: C, 60.37; H, 4.26; N, 0.00; Found: C, 60.23; H, 4.35; N, 0.00.

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. customdried in vacuo at 64° C. for 25 hours

出典と根拠

ORDレコード
ord-e6878d6335194100b007a5b207769fe9
出典データセット
uspto-grants-2007_01
特許番号
US07163954B2

反応ノート

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