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Ethyl isobutyrate → 2-(6-Methoxy-pyridin-2-yl)-2-methyl-propionic acid ethyl ester

HRID 61893
ノート
印刷プレビュー

反応式

HRID 61893 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.[C:10]([O:15][CH2:16][CH3:17])(=[O:14])[CH:11]([CH3:13])[CH3:12].C1COCC1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1(C)C=CC=CC=1.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].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[CH2:16]([O:15][C:10](=[O:14])[C:11]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1)([CH3:13])[CH3:12])[CH3:17]
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

9

反応物 4

HCID 7342Ethyl isobutyrateHCID 8028TetrahydrofuranHCID 2568102-Bromo-6-methoxypyridineHCID 2733832Lithium hexamethyldisilazane

生成物 1

HCID 668349252-(6-Methoxy-pyridin-2-yl)-2-methyl-propionic acid ethyl ester収率 64.4%

試薬・触媒・溶媒 4

HCID 83681
Tris(1,1-dimethylethyl)phosphine
触媒
HCID 9811564Bis(dibenzylideneacetone)palladium触媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

2-Bromo-6-methoxypyridine (7.0 g), ethyl isobutyrate (4.75 g), tri t-butylphosphine (300 mg) and Pd2(dba)3 (680 mg) were dissolved in toluene (200 ml) under nitrogen atmosphere, added with THF solution of LiHMDS (1.6 M, 24 ml), and the mixture was stirred at 100° C. for 6 hrs. The reaction mixture was diluted with ethyl acetate (300 ml), and washed three times with 15% brine (200 ml). The organic layer was concentrated under reduced pressure and the resulting residues were purified by silica gel column (n-hexane/ethyl acetate=4/1) to obtain the title compound (5.353 g, yield 60%).

後処理

  1. washwashed three times with 15% brine (200 ml)
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe resulting residues were purified by silica gel column (n-hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-e6f1d85672d846248de4662bd3f783e2
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09440922B2

反応ノート

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