Triphenylphosphine → methyl 2-[4-[((3R)-tetrahydro-3-furanyl)oxy]phenyl]-2-oxoacetate

HRID 361910

反応式

HRID 361910 の反応式
[OH:1][C@H:2]1[CH2:6][CH2:5][O:4][CH2:3]1.O[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[O:4]1[CH2:5][CH2:6][C@@H:2]([O:1][C:8]2[CH:9]=[CH:10][C:11]([C:14](=[O:19])[C:15]([O:17][CH3:18])=[O:16])=[CH:12][CH:13]=2)[CH2:3]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733227(S)-(+)-3-HydroxytetrahydrofuranHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

生成物 1

HCID 53727378methyl 2-[4-[((3R)-tetrahydro-3-furanyl)oxy]phenyl]-2-oxoacetate収率 54%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In 30 ml of tetrahydrofuran were dissolved 3.0 g of (S)-(+)-3-hydroxytetrahydrofuran, 6.6 g of methyl 2-(4-hydroxyphenyl)-2-oxoacetate and 8.90 g of triphenylphosphine. The thus prepared solution was mixed with 6.0 g of diethyl azodicarboxylate, and the mixture was stirred for 2 hours. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using chloroform as an eluant, thereby obtaining 4.60 g of methyl 2-[4-[((3R)-tetrahydro-3-furanyl)oxy]phenyl]-2-oxoacetate in an oily form.

後処理

  1. distillationAfter distilling off the solvent
  2. customthe resulting residue was purified

出典と根拠

ORDレコード
ord-70d79a8f795444b4b1f602b2ed4a59d7
出典データセット
uspto-grants-1999_02
特許番号
US05866577

関連ノート

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