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

HRID 619638
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HRID 619638 반응식
[CH2:1]([C:3]1[S:7][C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[C:19][C:20]4[CH:30]=[CH:29][C:23]([C:24]([O:26]CC)=[O:25])=[CH:22][CH:21]=4)[CH:16]=3)[S:11][C:10]([CH3:32])([CH3:31])[CH:9]=2)=[CH:5][CH:4]=1)C.C(C1(C2C3C(=CC=C(C#CC4C=CC(C(OCC)=O)=CC=4)C=3)SC(C)(C)C=2)CC=CS1)C.[OH-].[Na+].Cl>C1COCC1.CCO>[CH3:1][C:3]1[S:7][C:6]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][CH2:19][C:20]4[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:29][CH:30]=4)[CH:16]=3)[S:11][C:10]([CH3:32])([CH3:31])[CH:9]=2)=[CH:5][CH:4]=1
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참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21846694ethyl 4-[[4-(5-ethylthiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoateHCID 86754562HCID 86754562, 화합물

생성물 1

HCID 218466784-[[4-(5-methyl-thiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethyl]benzoic acid수율 73.7%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl 4-[[4-(5-ethylthiophen-2-yl)-2,2-dimethyl-(2H)-thiochromen-6-yl]-ethynyl]-benzoate (Compound 231, 23.0 mg, 0.05 mmol) in 1.0 mL THF and 1.0 mL EtOH was added NaOH (40.0 mg, 1.0 mmol, 1.0 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 15.5 mg (72%) of the title compound as an orange solid. 1H NMR (300 MHz, d6 -acetone) δ: 8.03 (2H, d, J=8.3 Hz), 7.63 (2H, d, J=8.3 Hz), 7.61 (1H, s), 7.44 (2H, s), 6.90 (1H, d, J=3.5 Hz), 6.83 (1H, d, J=3.5 Hz), 6.10 (1H, s), 2.86 (2H, q, J=7.6 Hz), 1.45 (6H, s), 1.30 (3H, t, J=7.6 Hz).

후처리

  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

출처 및 근거

ORD 기록
ord-c486651665d34fe09127ea2cf088f24d
출처 데이터셋
uspto-grants-1999_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05958954

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