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

HRID 1796615노트

반응식

HRID 1796615 반응식
[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]

참가 물질

7

반응물 5

HCID 11776Triphenylphosphine2회HCID 118940tert-Butyl 2-hydroxyisobutyrateHCID 165337IsobutyrateHCID 3016048o-(p-Nitrophenoxy)phenolHCID 5462977Diethyl azodicarboxylate2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-7be8e4e7d7ea4c73949608c8f95220e9
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030112B2

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