Benzoic Acid → Cyano-(2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-ylidene)acetic Acid Ethyl Ester

HRID 2228341ノート

反応式

HRID 2228341 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=O)[CH2:7][C:6]2([CH3:16])[CH3:15].[CH3:17][CH2:18][O:19][C:20]([CH2:22][C:23]#[N:24])=[O:21].N1CCCCC1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:18]([O:19][C:20](=[O:21])[C:22]([C:23]#[N:24])=[C:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([O:12][CH3:13])[CH:10]=2)[C:6]([CH3:16])([CH3:15])[CH2:7]1)[CH3:17]

参加物

6

反応物 4

HCID 243Benzoic AcidHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 138129z1-Indanone, 5,6-dimethoxy-3,3-dimethyl-

生成物 1

HCID 54568492Cyano-(2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-ylidene)acetic Acid Ethyl Ester収率 71.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

122 g (0.55 mol) of 2,3-Dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-one (CAS N.[4136-26-9] for preparation see F. Camps, Z. Naturforsch., B : Anorg. Chem., Org. Chem. (1984), 39B (12), 1801-5), 63,3 g (0.56 mol) of ethyl cyano acetate, 12 g (0.14 mol of piperidine, 12 g (0.1 mol) of benzoic acid and 1000 ml toluene were mixed together and heated under reflux for 48 hours. The reaction mixture was cooled to room temperature, washed with diluted HCl, aqueous Na2CO3, and water and then dried (MgSO4). Removal of the solvent and crystallization from EtOH gave 123.8 g of a yellow solid (m.p.: 148-149° C). Yield: 71%; E1%cm: 790 (1 max.: 367 nm) in EtOH. Solubility: 0.35% in CÉTIOL LC

後処理

  1. custom[4136-26-9] for preparation
  2. temperatureheated
  3. temperatureunder reflux for 48 hours
  4. washwashed with diluted HCl, aqueous Na2CO3, and water
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent and crystallization from EtOH

出典と根拠

ORDレコード
ord-6780460036344928ad4af2cb78f0fba1
出典データセット
uspto-grants-2002_07
特許番号
US06416746B1

反応ノート

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