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

HRID 1420755

反応式

HRID 1420755 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]([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: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 178418397HCID 178418397、化合物触媒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(0) (0.35 g) were added and the mixture was heated under reflux under a nitrogen atmosphere for 48 hours. Further tetrakis(triphenylphosphine)palladium(0) (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-efbe90a7f78546fcac0fa747596e88cc
出典データセット
uspto-grants-2000_06
特許番号
US06071938

関連ノート

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