Hydrochloric Acid → HCID 20482806、化合物

HRID 648251

反応式

HRID 648251 の反応式
C([N-]C1CCCCC1)(C)C.[Li+].[CH3:12][C:13]([CH3:32])=[CH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)=[O:16].[Br:33]Br.Cl>C1COCC1.CCOCC.CN(P(N(C)C)(N(C)C)=O)C>[Br:33][CH:14]([C:13]([CH3:32])=[CH2:12])[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)=[O:16]

参加物

8

反応物 4

HCID 313Hydrochloric Acid2 回HCID 24408BromineHCID 10877271Lithium cyclohexylisopropylamideHCID 20482725(3-Phenoxyphenyl)methyl 3-methylbut-2-enoate

生成物 1

HCID 20482806HCID 20482806、化合物

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 12679Hexamethylphosphoramide溶媒

実験手順

A 100 ml flask is flushed with nitrogen and to it is added 25 ml of a 1 M THF solution of lithium N-isopropylcyclohexylamide (0.025 mole) followed by HMPT (5 ml). The flask is cooled to -78° and 7.1 g (0.025 mole) of m-phenoxybenzyl 3-methyl-2-butenoate in THF (25 ml) is added dropwise over 5 minutes. After the addition the mixture is stirred at -20° for 1 hour. This cold solution is then added dropwise to 1.1 equivalent of bromine in THF at -78°. After a further 1 hour at -78°, 5 ml of concentrated hydrochloric acid is added and the mixture allowed to come to RT and poured into ether plus cold aqueous hydrochloric acid. The ether layer is washed with water and brine and dried over calcium sulfate. Removal of the solvent gives m-phenoxybenzyl 2-bromo-3-methyl-3-butenoate, which is reacted with p-methylaniline by the process of Example 5 to give m-phenoxybenzyl ester of 2-(p-methylphenylamino)-3-methyl-3-butenoate.

後処理

  1. customA 100 ml flask is flushed with nitrogen and to it
  2. temperatureThe flask is cooled to -78°
  3. additionAfter the addition the mixture
  4. waitAfter a further 1 hour at -78°
  5. customto come to RT
  6. washThe ether layer is washed with water and brine
  7. dry with materialdried over calcium sulfate
  8. customRemoval of the solvent

出典と根拠

ORDレコード
ord-b800be58ef504390999398529cc10f76
出典データセット
uspto-grants-1983_10
特許番号
US04411912

関連ノート

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