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

HRID 128779

반응식

HRID 128779 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-342bcfb170dd446095d890ba2b2078d3
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464865

연결된 노트

불러오는 중…