N-Hydroxyphthalimide → Benzyl 5-[3-(1,3-dioxoisoindolin-2-yloxy)propoxy]-3-chlorobenzoate

HRID 1698860ノート

反応式

HRID 1698860 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][OH:22])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:43]1[C:47](=[O:48])[C:46]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:45]2[C:44]1=[O:53].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[O:53]=[C:44]1[C:45]2[C:46](=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:47](=[O:48])[N:43]1[O:22][CH2:21][CH2:20][CH2:19][O:18][C:16]1[CH:17]=[C:2]([Cl:1])[CH:3]=[C:4]([CH:15]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

参加物

6

反応物 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18322176Benzyl 3-chloro-5-(3-hydroxypropoxy)benzoate

生成物 1

HCID 18322169Benzyl 5-[3-(1,3-dioxoisoindolin-2-yloxy)propoxy]-3-chlorobenzoate収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of alcohol 26 (5.96 g, 18.6 mmol), triphenylphosphine (5.40 g, 20.5 mmol), and N-hydroxyphthalirnide (2.10 g, 20.5 mmol) in tetrahydrofuran (186 mL) was cooled to 0° C. and reacted slowly with diethyl azodicarboxylate (3.50 mL, 22.3 mmol). After warming to ambient temperature and stirring 16 hrs, the reaction was concentrated in vacuo and purified by chromatography on silica gel (10% ethyl acetate in hexanes) giving product 27 (5.18 g, 60%). 1H NMR (300 MHz, CDCl3) δ 7.83 (dd, 2H, J=5.6 Hz, 3.1 Hz), 7.75 (dd, 2H, J=5.6 Hz, 3.1 Hz), 7.63 (t, 1H, J=1.5 Hz), 7.51 (dd, 1H, J=2.4 Hz, 1.4 Hz), 7.40 (m, 5H), 7.12 (t, 1H, J=2.3 Hz), 5.35 (s, 2H), 4.41 (t, 2H, J=6.1 Hz), 4.28 (t, 2H, J=6.1 Hz), 2.25 (pentet, 2H, J=6.1 Hz).

後処理

  1. concentrationthe reaction was concentrated in vacuo
  2. custompurified by chromatography on silica gel (10% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-8250fae45fd7470892bbf7e209111e20
出典データセット
uspto-grants-2002_02
特許番号
US06344466B2

反応ノート

読み込み中…