Triphenylphosphine → 2-Methyl-2-[2-(4-nitro-phenoxy)-phenoxy]-propionic acid tert-butyl ester

HRID 1796615ノート

反応式

HRID 1796615 の反応式
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[C:38]([CH3:47])([CH3:46])[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].CCOC(/N=N/C(OCC)=O)=O.C([O-])(=O)C(C)C>C1COCC1>[C:42]([O:41][C:39](=[O:40])[C:38]([CH3:47])([O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][C:7]1[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:46])([CH3:45])([CH3:44])[CH3:43]

参加物

7

反応物 5

HCID 11776Triphenylphosphine2 回HCID 118940tert-Butyl 2-hydroxyisobutyrateHCID 165337IsobutyrateHCID 3016048o-(p-Nitrophenoxy)phenolHCID 5462977Diethyl azodicarboxylate2 回

生成物 1

HCID 210251752-Methyl-2-[2-(4-nitro-phenoxy)-phenoxy]-propionic acid tert-butyl ester収率 95.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 388A (1.70 g, 7.35 mmol) and PPh3 (5.80 g, 22.1 mmol) in anhydrous THF (35 ml) was added t-butyl 2-hydroxyisobutyrate (3.83 ml, 22.1 mmol) followed by DEAD (3.47 ml, 22.1 mmol), the reaction mixture was stirred at rt for 19 h. More reagents PPh3 (1.16 g, 4.41 mmol), isobutyrate (0.77 ml, 4.41 mmol) and DEAD (0.69 ml, 4.41 mmol) were added, and the mixture was stirred for another 50 h, concentrated and purified by silica gel flash column chromatography to afford 388B (2.62 g, 96%) as a light pink crystalline solid (50%-80% CH2Cl2-hexanes).

後処理

  1. stirringthe mixture was stirred for another 50 h
  2. concentrationconcentrated
  3. custompurified by silica gel flash column chromatography

出典と根拠

ORDレコード
ord-7be8e4e7d7ea4c73949608c8f95220e9
出典データセット
uspto-grants-2006_04
特許番号
US07030112B2

反応ノート

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