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

HRID 2207198
ノート
印刷プレビュー

反応式

HRID 2207198 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒
HCID 6505921
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
触媒
HCID 1140Toluene溶媒2 回

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-15fcde66a99b4ee0bc4565b75a632c25
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09376387B2

反応ノート

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