Triphenylphosphine → 2-oxo-2H-1-benzopyran-7-yl 4-methoxycarbonyloxybenzoate

HRID 2120514ノート

反応式

HRID 2120514 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:20][C:21]1[CH:30]=[C:29]2[C:24]([CH:25]=[CH:26][C:27](=[O:31])[O:28]2)=[CH:23][CH:22]=1.[CH3:32][O:33][C:34]([O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[CH:39][CH:38]=1)=[O:35].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:32][O:33][C:34]([O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41]([O:20][C:21]2[CH:22]=[CH:23][C:24]3[CH:25]=[CH:26][C:27](=[O:31])[O:28][C:29]=3[CH:30]=2)=[O:42])=[CH:39][CH:38]=1)=[O:35]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5281426UmbelliferoneHCID 222422684-[(Methoxycarbonyl)oxy]benzoic acid

生成物 1

HCID 234351152-oxo-2H-1-benzopyran-7-yl 4-methoxycarbonyloxybenzoate収率 70.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

13.4 g triphenylphosphine is added to a solution of 8.3 g 7-hydroxycoumarin, 10.0 g 4-methoxycarbonyloxybenzoic acid, 8.9 g diethyl azodicarboxylate and 50 ml tetrahydrofuran at 0° C. The reaction mixture was stirred overnight at room temperature, filtered to remove inorganic material and the filtrate evaporated down, taken up in warm hexane, filtered to remove inorganic material and evaporated down again. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (1/1 v/v) as eluent and recrystallisation from acetonitrile to yield 12.2 g of 2-oxo-2H-1-benzopyran-7-yl 4-methoxycarbonyloxybenzoate.

後処理

  1. filtrationfiltered
  2. customto remove inorganic material
  3. customthe filtrate evaporated down
  4. filtrationfiltered
  5. customto remove inorganic material
  6. customevaporated down again
  7. customThe residue is purified by column chromatography on silica gel
  8. customrecrystallisation from acetonitrile

出典と根拠

ORDレコード
ord-12c2b528fafa40829cf1317985f30be4
出典データセット
uspto-grants-2004_02
特許番号
US06692797B1

反応ノート

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