Diiodomethane → HCID 18182224、化合物

HRID 1359412ノート

反応式

HRID 1359412 の反応式
N[C:2]1[S:6][C:5]2[CH2:7][CH:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:9][CH2:10][C:4]=2[C:3]=1[C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ICI.N(OCCC(C)C)=O.[BH4-].[Na+]>C(O)C.C(OCC)(=O)C.O1CCCC1>[OH:23][CH:16]([C:3]1[C:4]2[CH2:10][CH2:9][CH:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][C:5]=2[S:6][CH:2]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

8

反応物 4

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 4311764Sodium borohydrideHCID 181821752-Amino-3-benzoyl-6-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thiophene

生成物 1

HCID 18182224HCID 18182224、化合物収率 54.2%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 21.5 g of 2-amino-3-benzoyl-6-ethoxycarbonyl-4,5,6,7-tetrahydrobenzo[b]thiophene, 12.5 g of cuprous iodide, 26.3 ml of diiodomethane, 26.3 ml of isopentyl nitrite and 250 ml of tetrahydrofuran was heated under reflux for 1.5 hours. After cooling as it was, 500 ml of ethyl acetate was added to the reaction solution. The insoluble matters were filtered off, the mixture was subjected to silica gel column chromatography, and eluted with hexane and then with hexane/ethyl acetate (10:1), to give 17.4 g of a crude product. 1.5 g of sodium borohydride was added little by little to a solution of 200 ml of ethanol containing 17.4 g of this crude product under ice-cooling. After stirring at room temperature for one hour, the solvent was removed. Ethyl acetate and water were added to the residue, followed by extracting with ethyl acetate. The organic phase was washed with brine and the solvent was removed. The residue was subjected to silica gel column chromatography, and eluted with hexane and then with hexane/ethyl acetate (4:1), to give 11.2 g of the target compound.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling as it
  4. filtrationThe insoluble matters were filtered off
  5. washeluted with hexane
  6. customwith hexane/ethyl acetate (10:1), to give 17.4 g of a crude product
  7. temperaturecooling
  8. customthe solvent was removed
  9. additionEthyl acetate and water were added to the residue
  10. extractionby extracting with ethyl acetate
  11. washThe organic phase was washed with brine
  12. customthe solvent was removed
  13. washeluted with hexane

出典と根拠

ORDレコード
ord-1e0197eb128d437dbe1dd3030b6364ba
出典データセット
uspto-grants-2003_07
特許番号
US06599917B1

反応ノート

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