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2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → 7-Methoxy-3-(3-methoxymethoxy-pyridin-4-yl)-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

HRID 2275284
ノート
印刷プレビュー

反応式

HRID 2275284 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[O:15])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.I[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[O:23][CH2:24][O:25][CH3:26].CC(C)([O-])C.[Na+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>C(OCC)(=O)C.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][C:18]=3[O:23][CH2:24][O:25][CH3:26])[C:9](=[O:15])[C:10]2([CH3:13])[CH3:14])=[CH:5][CH:4]=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

8

反応物 4

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 129558244-Iodo-3-(methoxymethoxy)pyridineHCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one2 回HCID 23676156Sodium t-butoxide

生成物 1

HCID 668351667-Methoxy-3-(3-methoxymethoxy-pyridin-4-yl)-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one収率 47.4%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

To 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 924 mg), 4-iodo-3-methoxymethoxy-pyridine (1 g), sodium t-butoxide (906 mg), Pd2dba3 (173 mg) and S-Phos (185 mg), toluene (19 ml) was added, and the mixture was stirred and heated at 70° C. for 2 hrs under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate and filtered through Celite. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (610 mg, 47%).

後処理

  1. filtrationfiltered through Celite
  2. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residues were purified by silica gel column (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-ae28e539bb964aaf8612b3fa52c539c3
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09126931B2

反応ノート

読み込み中…

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