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

HRID 1796615Notes

Reaction equation

HRID 1796615 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-7be8e4e7d7ea4c73949608c8f95220e9
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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