18-Crown-6 → 1-(2-Methoxyethenyl)-4-(octyloxy)benzene

HRID 128779

反応式

HRID 128779 の反応式
CC(C)([O-])C.[K+].[Cl-].[CH3:8][O:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1.[CH2:48]([O:56][C:57]1[CH:64]=[CH:63][C:60]([CH:61]=O)=[CH:59][CH:58]=1)[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]>C1COCC1.CCCCCC>[CH3:8][O:9][CH:10]=[CH:61][C:60]1[CH:63]=[CH:64][C:57]([O:56][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:58][CH:59]=1

参加物

7

反応物 4

HCID 2855718-Crown-6HCID 90358p-(Octyloxy)benzaldehydeHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 537755121-(2-Methoxyethenyl)-4-(octyloxy)benzene

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

Potassium t-butoxide (1.9 g) is added to a slurry of methoxymethyl triphenylphosphonium chloride (6.17 g) and 18-Crown-6 (100 mg) in dry THF (40 ml). The mixture is stirred for 5 min, cooled to 15°, and a solution of 4-octyloxybenzaldehyde (3.52 g) in THF (5 ml) is added dropwise. The reaction mixture is stirred at room temperature for 20 min, diluted with 250 ml hexane, and the resulting mixture filtered through a pad of diatomaceous earth. Evaporation of the filtrate leaves crude 1-(2-methoxyethenyl)-4-(octyloxy)benzene as a mixture of cis and trans isomers, containing about 15 mol % triphenylphosphine oxide. The crude material may be used as is, or may be chromatographed with 1:1 hexanedichloromethane.

後処理

  1. temperaturecooled to 15°
  2. stirringThe reaction mixture is stirred at room temperature for 20 min
  3. filtrationthe resulting mixture filtered through a pad of diatomaceous earth
  4. customEvaporation of the filtrate

出典と根拠

ORDレコード
ord-342bcfb170dd446095d890ba2b2078d3
出典データセット
uspto-grants-1995_11
特許番号
US05464865

関連ノート

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