Hexamethylphosphoramide → 4-hydroxy-3-(phenylsulfanyl)-2H-chromen-2-one

HRID 2413328

反応式

HRID 2413328 の反応式
CN(C)P(=O)(N(C)C)N(C)C.Br[C:13]1[C:14](=[O:24])[O:15][C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=2.[C:25]1([S:31][Si](C)(C)C)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[C:25]1([S:31][C:13]2[C:14](=[O:24])[O:15][C:16]3[C:21]([C:22]=2[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

5

反応物 3

HCID 12679HexamethylphosphoramideHCID 78312PhenylthiotrimethylsilaneHCID 546821243-bromo-4-hydroxy-2H-chromen-2-one

生成物 1

HCID 546846444-hydroxy-3-(phenylsulfanyl)-2H-chromen-2-one収率 70.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1 ml of hexamethylphosphoric triamide and 1.0 g (4.15 mmoles) of 3-bromo-4-hydroxycoumarin were added to a solution of 0.91 g (5.0 mmoles) of phenylthio(trimethyl)silane in 25 ml of dry acetonitrile. After refluxing for 1 hour, the mixture was evaporated and the residue was dissolved in 125 ml of ethyl acetate. The solution obtained was washed twice with 125 ml of water and the ethyl acetate layer was dried and evaporated to dryness. The solid residue was washed with 100 ml of heptane and then with three portions of 50% ethanol, was vacuum dried at 40° C. to obtain 0.79 g (70.5% yield) of 3-phenylthio-4-hydroxycoumarin melting at 186°-189° C.

後処理

  1. temperatureAfter refluxing for 1 hour
  2. customthe mixture was evaporated
  3. dissolutionthe residue was dissolved in 125 ml of ethyl acetate
  4. customThe solution obtained
  5. washwas washed twice with 125 ml of water
  6. dry with materialthe ethyl acetate layer was dried
  7. customevaporated to dryness
  8. washThe solid residue was washed with 100 ml of heptane
  9. customdried at 40° C.

出典と根拠

ORDレコード
ord-e41b81b9509f472eb1d49757b376fbb9
出典データセット
uspto-grants-1985_01
特許番号
US04496720

関連ノート

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