Triphenylphosphine → Methyl 2-[3-(2-(carbazol-9-yl)ethoxy)phenylthio]isobutyrate

HRID 2223313

反応式

HRID 2223313 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([S:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH:16]1[C:28]2[N:27]([CH2:29][CH2:30]O)[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH:25]1[C:26]2[N:27]([CH2:29][CH2:30][O:1][C:2]3[CH:3]=[C:4]([S:8][C:9]([CH3:15])([CH3:14])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=3)[C:28]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]=2[CH:22]=[CH:23][CH:24]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 228287Carbazole-9-ethanolHCID 5363146Diisopropyl azodicarboxylateHCID 68621947Methyl 2-(3-hydroxyphenylthio)isobutyrate

生成物 1

HCID 10025091Methyl 2-[3-(2-(carbazol-9-yl)ethoxy)phenylthio]isobutyrate収率 45%

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-(3-hydroxyphenylthio)iso-butyrate (prepared as described in example 1) (0.609 g, 2.7 mmol), 9H-carbazol-9-ethanol (0.570 g, 2.7 mmol), DIAD (0.708 g, 3.5 mmol), and triphenylphosphine (0.917 g, 3.5 mmol) added piecemeal in small portions, keeping the temperature below 30° C., in 14 mL of anhydrous THF. The reaction was left under magnetic stirring for 18 hours at room temperature. After this period, the solvent was evaporated and the residue purified by silica gel chromatography using hexane/AcOEt 9/1 as eluent. 0.510 g of product were obtained (yield: 45%); Mp: 101-103° C.; TLC: silica gel, eluent hexane/AcOEt 8/2, Fr: 0.38; 1H NMR (CDCl3, 300 MHz) δ: 8.05 (d, 2H), 7.50 (m, 4H), 7.15 (m, 2H), 7.08 (t, 1H), 7.00 (d, 1H), 6.90 (s, 1H), 6.80 (m, 1H), 4.75 (t, 2H), 4.35 (t, 2H), 3.60 (s, 3H), 1.40 (s, 6H); HPLC: Column: Symmetry—C18, (5 μm) 4.6×150 mm, T: room temperature, mobile phase CH3CN/H2O 65/35 (v/v), pH: as is, flow rate: 0.80 mL/min, 205 nm UV detector, retention time 11.45 min; E.A. conforming for C25H25NO3S.

後処理

  1. additionadded piecemeal in small portions
  2. customthe temperature below 30° C.
  3. waitThe reaction was left
  4. waitAfter this period
  5. customthe solvent was evaporated
  6. customthe residue purified by silica gel chromatography

出典と根拠

ORDレコード
ord-0fa7c68a04c649569bc661463ffa647d
出典データセット
uspto-grants-2008_05
特許番号
US07375124B2

関連ノート

読み込み中…