Triphenylphosphine → Methyl 2-[4-[2-(4-chloro-phenyl)ethoxy]phenylthio]isobutyrate

HRID 2223310Notes

Reaction equation

HRID 2223310 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[Cl:16][C:17]1(OCC)[CH:22]=[CH:21][C:20](O)=[CH:19][CH2:18]1.[CH3:27][CH2:28]OC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:27][CH2:28][O:1][C:2]2[CH:7]=[CH:6][C:5]([S:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 673211524-Chlorophenetyl alcoholHCID 68620583Methyl 2-(4-hydroxyphenyl-thio)isobutyrate

Product 1

HCID 9799200Methyl 2-[4-[2-(4-chloro-phenyl)ethoxy]phenylthio]isobutyrateYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title product was prepared according to the procedure described in Method B starting from methyl 2-(4-hydroxyphenylthio)isobutyrate (prepared as described above) (0.800 g, 3.54 mmol) and 4-chlorophenetyl alcohol (0.554 g, 3.54 mmol) in 20 mL of anhydrous THF. DEAD (0.801 g, 4.6 mmol) and triphenylphosphine (1.205 g, 4.6 mmol) were added piecemeal in small portions, maintaining the temperature below 30° C. The reaction was left overnight under magnetic stirring at room temperature. After this period, the solvent was evaporated and the residue purified by silica gel chromatography using hexane/ethyl acetate 9/1 as eluent. 0.416 g of oily product were obtained (yield: 32%); TLC: silica gel, eluent hexane/ethyl acetate 9/1, Fr: 0.32; 1H NMR (CDCl3, 300 MHz) δ: 7.40-7.19 (m, 6H), 6.80 (d, 2H), 4.15 (t, 2H), 3.65 (s, 3H), 3.08 (t, 2H) 1.45 (s, 6H); HPLC: Column: Symmetry—C18, (5 μm) 4.6×250 mm, T: 30° C., mobile phase CH3CN/H2O 70/30 (v/v), pH: as is, flow rate: 0.75 mL/min, 205 nm UV detector, retention time 31.40 min; KF: 0.4% H2O; E.A. conforming for C19H21ClO3S.

Workup

  1. temperaturemaintaining the temperature below 30° C
  2. waitAfter this period
  3. customthe solvent was evaporated
  4. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-9c3784883dc9400894b3910cf7776251
Source dataset
uspto-grants-2008_05
Patent number
US07375124B2

Reaction notes

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