Lithium iodide → 6-(4-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

HRID 1420757

반응식

HRID 1420757 반응식
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:22]=[CH:21][C:13]3[O:14][C:15]([CH3:20])([CH3:19])[C:16]([CH3:18])=[CH:17][C:12]=3[CH:11]=2)=[CH:5][CH:4]=1.[I-].[Li+]>N1C(C)=CC(C)=CC=1C.ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([S:9][C:10]2[CH:22]=[CH:21][C:13]3[O:14][C:15]([CH3:19])([CH3:20])[C:16]([CH3:18])=[CH:17][C:12]=3[CH:11]=2)=[CH:7][CH:8]=1

참가 물질

5

반응물 2

HCID 66321Lithium iodide2회HCID 187828716-(4-methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

생성물 1

HCID 187828866-(4-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran수율 77.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 79532,4,6-Trimethylpyridine용매

실험 절차

6-(4-Methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (7.816 g) (see Preparation 5) was dissolved in dry 2,4,6-collidine (30 ml), anhydrous lithium iodide (10.04 g) was added and the mixture was heated under reflux under a nitrogen atmosphere for 48 hours. A further portion of lithium iodide (9.06 g). was then added and heating was continued for another 72 hours. After cooling, the mixture was taken up in dichloromethane and washed with 2N aqueous hydrochloric acid solution (×3). The organic layer was separated, dried (anhydrous sodium sulphate), the solvent removed under reduced pressure and the residue was chromatographed on silica using dichloromethane as the eluent to yield 6-(4-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (5.799 g) as an oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under a nitrogen atmosphere for 48 hours
  3. additionwas then added
  4. temperatureheating
  5. temperatureAfter cooling
  6. washwashed with 2N aqueous hydrochloric acid solution (×3)
  7. customThe organic layer was separated
  8. dry with materialdried (anhydrous sodium sulphate)
  9. customthe solvent removed under reduced pressure
  10. customthe residue was chromatographed on silica

출처 및 근거

ORD 기록
ord-0070bc41127a4a2bb2703635e398c548
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06071938

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