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

HRID 1200089

反応式

HRID 1200089 の反応式
[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]

参加物

4

反応物 2

HCID 125074-MethoxystyreneHCID 186901361-Cyano-4-methoxybenzocyclobutene

生成物 1

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

試薬・触媒・溶媒 1

HCID 72391,2-Dichlorobenzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b29107429d714e9bbc6adb7e6e1872dc
出典データセット
uspto-grants-1990_02
特許番号
US04904661

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