Hydrochloric Acid → 4-(1-Indanyl)-1-butanol

HRID 2393484

反応式

HRID 2393484 の反応式
II.C1(=O)C2C(=CC=CC=2)CC1.BrC/C=C/C(OC)=O.Cl.[CH:22]1([CH:31]=[CH:32][CH2:33][CH2:34][OH:35])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23]1>O1CCCC1.CO.[H][H].[Pd].[Zn].ClCCl.CCOCC>[CH:22]1([CH2:31][CH2:32][CH2:33][CH2:34][OH:35])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23]1

参加物

12

反応物 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 67351-IndanoneHCID 53691752-Butenoic acid, 4-bromo-, methyl esterHCID 541606614-(1-Indanyl)-but-3-en-1-ol

生成物 1

HCID 220121884-(1-Indanyl)-1-butanol収率 98.9%

試薬・触媒・溶媒 6

HCID 23938Palladium触媒HCID 23994Zinc触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 21881112Ethyl ether methylene chloride溶媒HCID 178418361HCID 178418361、化合物溶媒

実験手順

A suspension of activated zinc (40 g) in dry tetrahydrofuran (150 ml) was heated to reflux and a few crystals of iodine was added. A solution of 1-indanone (50 g) and methyl 4-bromo-crotonate (100 g) in 400 ml of dry tetrahydrofuran was added dropwise followed by reflux for 1 h. After cooling, ice was added and the pH adjusted to 1 with concentrated hydrochloric acid followed by extraction with dichloromethane. Concentration of the organic phase left a viscous oil which was dissolved in methanol (400 ml). Concentrated hydrochloric acid (100 ml) was added and the mixture stirred for 30 min. Removal of solvents in vacuo, addition of water, and extraction with ether gave, after drying over magnesium sulfate and removal of solvent in vacuo, an oil (34 g). The oil was dissolved in 300 ml of dry ether and added dropwise to a suspension of lithium aluminium hydride (21g). After reflux for 2 h, the reaction mixture was hydrolyzed with water. Filtration and removal of solvent in vacuo gave a mixture of isomers from which 4-(1-indanyl)-but-3-en-1-ol (6 g) could be isolated by column chromatography (silica gel, eluent: dichloromethane/ether=9:1). The. remaining mixture of isomers (9 g) was dissolved in 150 ml of methanol and hydrogenated at 3 atm of hydrogen pressure in a conventional Parr apparatus in the presence of 5% palladium on charcoal (6 g) for 12 h. Filtration and removal of solvent in vacuo gave 6 g of 4-(1-indanyl)-1-butanol.

後処理

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureby reflux for 1 h
  4. temperatureAfter cooling
  5. additionice was added
  6. extractionfollowed by extraction with dichloromethane
  7. waitConcentration of the organic phase left a viscous oil which
  8. dissolutionwas dissolved in methanol (400 ml)
  9. additionConcentrated hydrochloric acid (100 ml) was added
  10. customRemoval of solvents
  11. additionin vacuo, addition of water, and extraction with ether
  12. customgave
  13. dry with materialafter drying over magnesium sulfate and removal of solvent in vacuo
  14. dissolutionThe oil was dissolved in 300 ml of dry ether
  15. additionadded dropwise to a suspension of lithium aluminium hydride (21g)
  16. temperatureAfter reflux for 2 h
  17. filtrationFiltration and removal of solvent in vacuo
  18. customgave
  19. additionmixture of isomers (9 g)
  20. filtrationFiltration and removal of solvent in vacuo

出典と根拠

ORDレコード
ord-43578274d63d4269915e852c1b5871c9
出典データセット
uspto-grants-1998_09
特許番号
US05807871

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