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

HRID 1416178

반응식

HRID 1416178 반응식
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

참가 물질

6

반응물 3

HCID 849893-MethoxybenzenethiolHCID 14956089HCID 14956089, 화합물HCID 23676156Sodium t-butoxide

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매2회HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-93d3b7e6ae6c47ad8c7c63f53a437795
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912244

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