Thioguaiacol → 6-(2-methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

HRID 1420756ノート

反応式

HRID 1420756 の反応式
Br[C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]([CH3:12])([CH3:11])[C:8]([CH3:10])=[CH:9][C:4]=2[CH:3]=1.CC(C)([O-])C.[Na+].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[SH:29]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]([CH3:12])([CH3:11])[C:8]([CH3:10])=[CH:9][C:4]=2[CH:3]=1

参加物

6

反応物 3

HCID 23642ThioguaiacolHCID 149560896-Bromo-2,2,3-trimethyl-2H-benzo[b]pyranHCID 23676156Sodium t-butoxide

生成物 1

HCID 187828656-(2-methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran収率 68.8%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒

実験手順

6-Bromo-2,2,3-trimethyl-2H-benzo[b]pyran (9.6 g) (see Preparation 4) was dissolved in absolute ethanol (200 ml), then sodium tert-butoxide (11.0 g), 2-methoxybenzenethiol (5.3 g) and tetrakis(triphenylphosphine)palladium(0) (0.45 g) were added and the mixture heated under reflux under a nitrogen atmosphere for 24 hours. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane and washed with water. The organic layer was dried (anhydrous sodium sulphate), the solvent was removed under reduced pressure and the crude product was chromatographed first on silica using 1:1 hexane:dichloromethane as the eluent and then on silica using 24:1 hexane:ethyl acetate as the eluent to yield 6-(2-methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (8.12 g) as an oil.

後処理

  1. temperaturethe mixture heated
  2. temperatureunder reflux under a nitrogen atmosphere for 24 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialThe organic layer was dried (anhydrous sodium sulphate)
  7. customthe solvent was removed under reduced pressure
  8. customthe crude product was chromatographed first on silica using 1:1 hexane

出典と根拠

ORDレコード
ord-7b41d0cc63fc4e5892490908b45eba3b
出典データセット
uspto-grants-2000_06
特許番号
US06071938

反応ノート

読み込み中…