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

HRID 1420756노트

반응식

HRID 1420756 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: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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7b41d0cc63fc4e5892490908b45eba3b
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06071938

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