Hydrochloric Acid → 4-[[4-(5-tert-butylthiopen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethyl]benzoic acid

HRID 619639ノート

反応式

HRID 619639 の反応式
[C:1]([C:5]1[S:9][C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[C:21][C:22]4[CH:32]=[CH:31][C:25]([C:26]([O:28]CC)=[O:27])=[CH:24][CH:23]=4)[CH:18]=3)[S:13][C:12]([CH3:34])([CH3:33])[CH:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1.CCO>[C:1]([C:5]1[S:9][C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][C:22]4[CH:32]=[CH:31][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=4)[CH:18]=3)[S:13][C:12]([CH3:34])([CH3:33])[CH:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846655Ethyl 4-[[4-(5-tert-butyl-thiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate2 回

生成物 1

HCID 1317213904-[[4-(5-tert-butylthiopen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethyl]benzoic acid収率 82%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl 4-[[4-(5-tert-butylthiophen-2-yl)-2,2-dimethyl(2H)-thiochromen-6-yl]-ethynyl]-benzoate (Compound 232, 88.0 mg, 0.181 mmol) in 2.0 mL THF and 2.0 mL EtOH was added NaOH (160.0 mg, 4.0 mmol, 4.0 mL of a 1M aqueous solution). The resulting solution was stirred overnight at room temperature. The reaction mixture was acidified with 10% aqueous HCl and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and dried (Na2SO4) before removing the solvent under reduced pressure. The residual solid was recrystallized from CH3CN to give 68.0 mg (82%) of the title compound as a pale-yellow solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.03 (2H, d, J=8.3 Hz), 7.63 (2H, d, J=8.3 Hz), 7.62 (1H, s), 7.44 (2H, d, J=1.2 Hz), 6.87 (2H, s), 6.11 (1H, s), 1.45 (6H, s), 1.39 (9H, s).

後処理

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  3. dry with materialdried (Na2SO4)
  4. custombefore removing the solvent under reduced pressure
  5. customThe residual solid was recrystallized from CH3CN

出典と根拠

ORDレコード
ord-5cf5f5ffdba442ea9d51371ac6d76d66
出典データセット
uspto-grants-1999_09
特許番号
US05958954

反応ノート

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