4-Methoxystyrene → (1RS,2SR)-1-cyano-1,2,3,4-tetrahydro-2-p-methoxyphenylnaphthalene

HRID 1493299

반응식

HRID 1493299 반응식
[C:1]([CH:3]1[C:6]2=[C:7](OC)[CH:8]=[CH:9][CH:10]=[C:5]2[CH2:4]1)#[N:2].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[CH2:20])=[CH:17][CH:16]=1>ClC1C=CC=CC=1Cl>[C:1]([CH:3]1[C:6]2[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:4][CH2:20][CH:19]1[C:18]1[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1)#[N:2]

참가 물질

4

반응물 2

HCID 125074-MethoxystyreneHCID 186901361-Cyano-4-methoxybenzocyclobutene

생성물 1

HCID 67945262(1RS,2SR)-1-cyano-1,2,3,4-tetrahydro-2-p-methoxyphenylnaphthalene

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

실험 절차

A solution of 1-cyano-4-methoxybenzocyclobutene (7.5 g.; described in the Journal of the American Chemical Society, 1976, 98, 8185) and p-methoxystyrene (11.1 g.) in o-dichlorobenzene (40 ml.) was heated under reflux for 30 minutes under an atmosphere of argon and then evaporated to dryness, and the residue was purified by chromatography on a silica gel column using a 20:1 v/v mixture of toluene and ethyl acetate as eluant. A mixture of a solution of the residue (12.0 g.) in toluene (200 ml.), a solution of sodium hydroxide (20 g.) in water (200 ml.) and 40% w/v aqueous tetrabutylammonium hydroxide solution (1 ml.) was stirred vigorously under an atmosphere of argon at laboratory temperature for 12 hours and the layers were then separated. The aqueous layer was extracted twice with diethyl ether (100 ml. each time) and the combined organic solutions were washed with water, dried and evaporated to dryness. There was thus obtained as residue (1RS,2SR)-1-cyano-1,2,3,4-tetrahydro-2-p-methoxyphenylnaphthalene, m.p. 126°-131° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes under an atmosphere of argon
  3. customevaporated to dryness
  4. customthe residue was purified by chromatography on a silica gel column
  5. additiona 20:1 v/v mixture of toluene and ethyl acetate as eluant
  6. additionA mixture of a solution of the residue (12.0 g.) in toluene (200 ml.)
  7. customthe layers were then separated
  8. extractionThe aqueous layer was extracted twice with diethyl ether (100 ml
  9. washeach time) and the combined organic solutions were washed with water
  10. customdried
  11. customevaporated to dryness

출처 및 근거

ORD 기록
ord-d029fdaf4d6546c39ceeb077a6caeb2d
출처 데이터셋
uspto-grants-1991_06
특허 번호
US05021414

연결된 노트

불러오는 중…