Tributylphosphine → 3-(4-{1-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic acid methyl ester

HRID 860675ノート

反応式

HRID 860675 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH:16]([OH:18])[CH3:17])=[C:11]([CH:13]([CH3:15])[CH3:14])[N:12]=2)=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[CH3:50][O:51][C:52](=[O:63])[CH2:53][CH2:54][C:55]1[CH:60]=[CH:59][C:58](O)=[CH:57][C:56]=1[CH3:62]>C1(C)C=CC=CC=1>[CH3:50][O:51][C:52](=[O:63])[CH2:53][CH2:54][C:55]1[CH:60]=[CH:59][C:58]([O:18][CH:16]([C:10]2[O:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)=[N:12][C:11]=2[CH:13]([CH3:15])[CH3:14])[CH3:17])=[CH:57][C:56]=1[CH3:62]

参加物

6

反応物 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 13551833Methyl 3-(4-Hydroxy-2-methylphenyl)propanoateHCID 587656641-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethanol

生成物 1

HCID 101521383-(4-{1-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic acid methyl ester収率 80.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 1-[2-(4-bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethanol (9.05 g, 29.2 mmol) in toluene (300 ml) at 0° C. is added tri-n-butylphosphine (7.70 g, 38.1 mmol) and 1,1′-(azodicarbonyl)-dipiperidine (8.84 g, 35.0 mmol), followed by addition of 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (6.30 g, 32.1 mmol). The resulting mixture is stirred for 18 hours while warmed up to room temperature. The reaction is quenched with water (100 ml) and the aqueous layer is extracted with EtOAc (2×100 ml). The combined organics are dried over Na2SO4 and concentrated, purified by silica gel chromatography (Hexanes/EtOAc, 9/1 to 8.5/1.5) to afford the 3-(4-{1-[2-(4-bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic acid methyl ester as a colorless oil (11.4 g, 80%). MS (MH+): 488.1.

後処理

  1. customThe reaction is quenched with water (100 ml)
  2. extractionthe aqueous layer is extracted with EtOAc (2×100 ml)
  3. dry with materialThe combined organics are dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (Hexanes/EtOAc, 9/1 to 8.5/1.5)

出典と根拠

ORDレコード
ord-c11460d8731d4ce0b09b859d5c024e73
出典データセット
uspto-grants-2006_12
特許番号
US07153878B2

反応ノート

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