Hydrochloric Acid → HCID 20482806, 화합물

HRID 648251

반응식

HRID 648251 반응식
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]

참가 물질

8

반응물 4

HCID 313Hydrochloric Acid2회HCID 24408BromineHCID 10877271Lithium cyclohexylisopropylamideHCID 20482725(3-Phenoxyphenyl)methyl 3-methylbut-2-enoate

생성물 1

HCID 20482806HCID 20482806, 화합물

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매3회HCID 12679Hexamethylphosphoramide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b800be58ef504390999398529cc10f76
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04411912

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