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Hydrochloric Acid → 3,4-Dihydro-1-(4-methylphenyl)-4,4-dimethyl-6-acetylnaphthalene

HRID 853192
ノート
印刷プレビュー

反応式

HRID 853192 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)=[CH:7][CH2:8][C:9]2([CH3:13])[CH3:12])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:26]([O:28]CC)=[CH2:27])CCC.Cl.C(OCC)(=O)C>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][C:9]1([CH3:13])[C:10]2[CH:11]=[C:2]([C:26](=[O:28])[CH3:27])[CH:3]=[CH:4][C:5]=2[C:6]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[CH:7][CH2:8]1
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 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 574238127-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydro-naphthalene2 回

生成物 1

HCID 223237763,4-Dihydro-1-(4-methylphenyl)-4,4-dimethyl-6-acetylnaphthalene収率 95%

試薬・触媒・溶媒 2

HCID 178418476
HCID 178418476、化合物
触媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A solution of 7-bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydro-naphthalene (Compound 4, 295 mg, 0.90 mmol) in 5 ml of THF was first degassed by bubbling with argon for 30 min. Tributyl(1-ethoxyvinyl)tin (650 mg, 1.80 mmol) and PdCl2(PPh3)2 (63 mg, 0.09 mmol) were added. After stirring at 80° C. for 18 h, the mixture was cooled to room temperature and 3 mL of 10% HCl was added. The mixture was then stirred for another 30 min before extraction with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (80:20 hexane/ethyl acetate) afforded the title compound (248 mg, 95% yield) as a colorless oil:

後処理

  1. customby bubbling with argon for 30 min
  2. temperaturethe mixture was cooled to room temperature
  3. washThe combined organic layer was washed with brine (1×10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated at reduced pressure
  6. customPurification by flash chromatography (80:20 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-49eb2f6c3d384ff28598574b44ece3bd
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07253319B2

反応ノート

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