Methanol → (RS)-2'-(2-oxoethyl)-5'-methoxy-2',3'-dihydro-spiro[cyclopentane-1,1'-[1H]indene]-3'-one

HRID 264492ノート

反応式

HRID 264492 の反応式
O=[O+][O-].[CH2:4]([CH:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[C:9]21[CH2:23][CH2:22][CH2:21][CH2:20]2)C=CC.[CH3:24][OH:25]>ClCCl>[O:25]=[CH:24][CH2:4][CH:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[C:9]21[CH2:20][CH2:21][CH2:22][CH2:23]2

参加物

5

反応物 3

HCID 887MethanolHCID 24823Ozone2 回HCID 53682889(RS)-2'-(2-buten-1-yl)-5'-methoxy-2',3'-dihydro-spiro[cyclopentane-1,1'-[1H]indene]-3'-one

生成物 1

HCID 19036586(RS)-2'-(2-oxoethyl)-5'-methoxy-2',3'-dihydro-spiro[cyclopentane-1,1'-[1H]indene]-3'-one収率 97%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

An ozone stream (2.5 g ozone/hour) was conducted for 50 minutes while stirring through a solution, cooled to -70°, of 6.2 g of (RS)-2'-(2-buten-1-yl)-5'-methoxy-2',3'-dihydro-spiro[cyclopentane-1,1'-[1H]indene]-3'-one in 80 ml of anhydrous dichloromethane and 20 ml of anhydrous methanol. Subsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes. After the addition of 2.52 ml of dimethyl sulfide, the mixture was stirred at room temperature for 17 hours. The reaction mixture was evaporated in a vacuum. The residue was treated with 100 ml of dichoromethane and, after the addition of 15 ml of water and 15 ml of trifluoroacetic acid, stirred at room temperature for 2.5 hours. The mixture was subsequently poured into 150 ml of water and neutralized by the spatula-wise addition of sodium hydrogen carbonate while stirring. An additional 50 ml of water were added. The phases were separated and the aqueous phase was extracted twice with 100 ml of dichloro-methane each time. The combined organic phases were dried over magnesium sulfate and concentrated in a vacuum. 5.74 g (97%) of (RS)-2'-(2-oxoethyl)-5'-methoxy-2',3'-dihydro-spiro[cyclopentane-1,1'-[1H]indene]-3'-one were obtained as a light yellow oil.

後処理

  1. customSubsequently, the solution was flushed with oxygen for 5 minutes and with argon for 10 minutes
  2. additionAfter the addition of 2.52 ml of dimethyl sulfide
  3. stirringthe mixture was stirred at room temperature for 17 hours
  4. customThe reaction mixture was evaporated in a vacuum
  5. additionThe residue was treated with 100 ml of dichoromethane
  6. additionafter the addition of 15 ml of water and 15 ml of trifluoroacetic acid
  7. stirringstirred at room temperature for 2.5 hours
  8. additionThe mixture was subsequently poured into 150 ml of water
  9. additionneutralized by the spatula-wise addition of sodium hydrogen carbonate
  10. stirringwhile stirring
  11. additionAn additional 50 ml of water were added
  12. customThe phases were separated
  13. extractionthe aqueous phase was extracted twice with 100 ml of dichloro-methane each time
  14. dry with materialThe combined organic phases were dried over magnesium sulfate
  15. concentrationconcentrated in a vacuum

出典と根拠

ORDレコード
ord-471cc22a4ba7401a9fbd81e1861c9741
出典データセット
uspto-grants-1997_07
特許番号
US05646173

反応ノート

読み込み中…