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

HRID 1416178

反応式

HRID 1416178 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:24]=[C:25]([SH:29])[CH:26]=[CH:27][CH:28]=1>C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:21][O:22][C:23]1[CH:24]=[C:25]([S:29][C:2]2[CH:14]=[CH:13][C:5]3[O:6][C:7]([CH3:12])([CH3:11])[C:8]([CH3:10])=[CH:9][C:4]=3[CH:3]=2)[CH:26]=[CH:27][CH:28]=1

参加物

6

反応物 3

HCID 849893-MethoxybenzenethiolHCID 14956089HCID 14956089、化合物HCID 23676156Sodium t-butoxide

生成物 1

HCID 187828766-(3-methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran収率 89.8%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒2 回HCID 702Ethanol溶媒

実験手順

6-Bromo-2,2,3-trimethyl-2H-benzo[b]pyran (6.5 g) (see Preparation 4) was dissolved in absolute ethanol (135 ml), then sodium tert-butoxide (7.5 g), 3-methoxybenzenethiol (3.6 g) and tetrakis(triphenylphosphine)palladium(O) (0.35 g) were added and the mixture was heated under reflux under a nitrogen atmosphere for 48 hours. Further tetrakis(triphenylphosphine)palladium(O) (0.3 g) was added and heating was continued for a further 48 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 removed under reduced pressure and the crude product chromatographed on silica using 1:1 hexane: dichloromethane as the eluent to yield 6-(3-methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (7.2 g) as an oil.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under a nitrogen atmosphere for 48 hours
  3. temperatureheating
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe residue was dissolved in dichloromethane
  6. washwashed with water
  7. dry with materialThe organic layer was dried (anhydrous sodium sulphate)
  8. customthe solvent removed under reduced pressure
  9. customthe crude product chromatographed on silica using 1:1 hexane

出典と根拠

ORDレコード
ord-93d3b7e6ae6c47ad8c7c63f53a437795
出典データセット
uspto-grants-1999_06
特許番号
US05912244

関連ノート

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