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

HRID 2223310노트

반응식

HRID 2223310 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-9c3784883dc9400894b3910cf7776251
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375124B2

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