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Hydrochloric Acid → 2-[(3-Acetyl-4-pyridyl)methyl]-6-methoxy-tetralin-1-one

HRID 2207198
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HRID 2207198 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]1=[O:21].[CH2:22]([O:24]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:23].Cl>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:22]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]1=[O:21])(=[O:24])[CH3:23]
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참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 1185580372-[(3-Bromo-4-pyridyl)methyl]-6-methoxy-tetralin-1-one

생성물 1

HCID 1185580142-[(3-Acetyl-4-pyridyl)methyl]-6-methoxy-tetralin-1-one수율 96%

시약·촉매·용매 3

HCID 11776Triphenylphosphine촉매
HCID 6505921
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
촉매
HCID 1140Toluene용매2회

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온도
110 °C

실험 절차

A toluene solution (9 mL) of compound 99 (1.0 g, 2.89 mmol), Pd(dba)2 (70 mg, 0.12 mmol) and PPh3 (30 mg, 0.12 mmol) was stirred at room temperature under argon for 15 min. Then, (1-ethoxyvinyl)tri(n-butyl)stannane (1.08 mL, 3.18 mmol) in toluene (6 mL) was added and the resulting mixture was stirred overnight at 110° C., cooled to room temperature and filtered on Celite, washed with EtOAc and concentrated under reduced pressure. Purification on silica gel (Petroleum ether 100% to EtOAc 100%) afford the product which was placed in presence of an aqueous solution of HCl 1M for 30 minutes at room temperature. After neutralization with a saturated aqueous solution of NaHCO3, aqueous phase was extracted with dichloromethane and the combined organic layers were dried over magnesium sulfate to afford the title compound 103 (Yield 475 mg, 96%) which was used without further purification.

후처리

  1. temperaturecooled to room temperature
  2. filtrationfiltered on Celite
  3. washwashed with EtOAc
  4. concentrationconcentrated under reduced pressure
  5. customPurification on silica gel (Petroleum ether 100% to EtOAc 100%)
  6. customafford the product which
  7. extractionAfter neutralization with a saturated aqueous solution of NaHCO3, aqueous phase was extracted with dichloromethane
  8. dry with materialthe combined organic layers were dried over magnesium sulfate

출처 및 근거

ORD 기록
ord-15fcde66a99b4ee0bc4565b75a632c25
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09376387B2

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