Tetrahydrofuran → {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetic acid

HRID 456842ノート

反応式

HRID 456842 の反応式
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH2:29][C:30]([O:32]C)=[O:31])[CH:22]=[CH:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[C@H](NCCC1C=CC(O)=CC=1)[C@H](O)C1C=CC(O)=CC=1.[OH-].[Na+].C1COCC1>O.CO>[C:1]1([N:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][CH:9]=[C:8]2[C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[C:23]([O:28][CH2:29][C:30]([OH:32])=[O:31])[CH:22]=[CH:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 33572RitodrineHCID 86603528methyl {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate

生成物 1

HCID 11618606{[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetic acid収率 90.5%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

In a similar manner as described in step 2 of Example 6, the title compound was prepared from methyl {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetate (0.17 g, 0.39 mmol), prepar in the previous step, and 1N NaOH (0.59 mL, 0.59 mmol) in 5:5:1 THF:MeOH:water (55 mL) with the exception that this reaction required heating to 65° C. and was complete after 6 hours. The still warm reaction mixture was filtered and then allowed to cool to ambient temperature. The mixture was acidified with 1N HCl (2.5 mL) and the volatiles were removed under reduced pressure (without the addition of heat). The resulting slurry was diluted with water (25 mL) and the solids were isolated by filtration to give {[6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthyl]oxy}acetic acid as an off-white solid (0.148 g, 90%), mp 258–260° C. (dec). Elemental Analysis for C28H21NO3.0.23 H2O Calc'd: C, 79.39; H, 5.11; N, 3.31. Found: C, 78.84; H 5.03; N, 3.00.

後処理

  1. customThe still warm reaction mixture
  2. filtrationwas filtered
  3. temperatureto cool to ambient temperature
  4. customthe volatiles were removed under reduced pressure (
  5. additionwithout the addition
  6. temperatureof heat)
  7. additionThe resulting slurry was diluted with water (25 mL)
  8. customthe solids were isolated by filtration

出典と根拠

ORDレコード
ord-d5a9add9b5fe4aaeba2b838b3950ea22
出典データセット
uspto-grants-2007_03
特許番号
US07186749B2

反応ノート

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