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

HRID 2223310ノート

反応式

HRID 2223310 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-9c3784883dc9400894b3910cf7776251
出典データセット
uspto-grants-2008_05
特許番号
US07375124B2

反応ノート

読み込み中…