Triphenylphosphine → HCID 140398709、化合物

HRID 1419727ノート

反応式

HRID 1419727 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:13]/[OH:14])/[C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8].[CH:15]([O:28][C:29]1[C:30](=[O:37])[CH:31]=[C:32]([CH2:35]O)[O:33][CH:34]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:13]/[O:14][CH2:35][C:32]1[O:33][CH:34]=[C:29]([O:28][CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:30](=[O:37])[CH:31]=1)/[C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 143063875-(benzhydryloxy)-2-(hydroxymethyl)-4H-pyran-4-oneHCID 15093893HCID 15093893、化合物

生成物 1

HCID 140398709HCID 140398709、化合物収率 207.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To an ice cooled solution of allyl (E)-2-(2-thienyl)-2-(hydroxyimino)acetate (1.0 gm, 4.734 mmol), 5-benzhydryloxy-2-(hydroxymethyl) pyran-4-one (1.46 gm, 4.734 mmol) and triphenylphosphine (1.24 gm, 4.734 mmol) in dry THF (30 ml) under nitrogen was added dropwise diethyl azodicarboxylate (820 μl, 5.208 mmol). The reaction mixture was stirred at room temperature overnight and concentrated under reduced pressure to afford the crude as yellow gum (4.93 gm). The product was purified by silica gel column chromatography using hexane-ethyl acetate (2:1) as eluant to provide the title compound as a gummy foam in 47% yield (1.11 gm).

後処理

  1. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7591388962854cca93938c3e132549b9
出典データセット
uspto-grants-1999_03
特許番号
US05888998

反応ノート

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