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

HRID 1420758

反応式

HRID 1420758 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1.[I-].[Li+]>N1C(C)=CC(C)=CC=1C.ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1

参加物

5

反応物 2

HCID 66321Lithium iodideHCID 187828766-(3-methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran

生成物 1

HCID 187828646-(3-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran収率 67.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 79532,4,6-Trimethylpyridine溶媒

実験手順

6-(3-Methoxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (3.5 g) (see Preparation 6) was dissolved in dry 2,4,6-collidine (15 ml), anhydrous lithium iodide (3 g) was added and the mixture was heated under reflux under a nitrogen atmosphere for 24 hours. After cooling, the mixture was taken up in dichloromethane and washed with 2N aqueous hydrochloric acid solution (×3). The-organic layer was dried (anhydrous sodium sulphate), the solvent removed under reduced pressure and the residue chromatographed on silica eluting with a solvent gradient of 1:1 hexane:dichloromethane changing to dichloromethane to yield 6-(3-hydroxyphenyl)thio-2,2,3-trimethyl-2H-benzo[b]pyran (2.25 g) as an oil.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux under a nitrogen atmosphere for 24 hours
  3. temperatureAfter cooling
  4. washwashed with 2N aqueous hydrochloric acid solution (×3)
  5. dry with materialThe-organic layer was dried (anhydrous sodium sulphate)
  6. customthe solvent removed under reduced pressure
  7. customthe residue chromatographed on silica eluting with a solvent gradient of 1:1 hexane

出典と根拠

ORDレコード
ord-fd53e3dbc15b4bf1bd0df7d7492227d9
出典データセット
uspto-grants-2000_06
特許番号
US06071938

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