Hydrogen Peroxide → 4-[1-(hydroxy)-4,4-dimethyl-2-octenyl]hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

HRID 247502

反応式

HRID 247502 の反応式
[CH3:1][C:2]([CH3:21])([CH2:17][CH2:18][CH2:19][CH3:20])[CH:3]=[CH:4][C:5]([CH:7]1[CH:14]2[CH:10]([O:11][C:12](=[O:15])[CH2:13]2)[CH2:9][CH:8]1[CH3:16])=[O:6].C([BH-](C(CC)C)C(CC)C)(CC)C.[K+].[OH-].[Na+].OO>C1COCC1>[OH:6][CH:5]([CH:7]1[CH:14]2[CH:10]([O:11][C:12](=[O:15])[CH2:13]2)[CH2:9][CH:8]1[CH3:16])[CH:4]=[CH:3][C:2]([CH3:1])([CH3:21])[CH2:17][CH2:18][CH2:19][CH3:20]

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 731845924-(4,4-dimethyl-1-oxo-2-octenyl)hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

生成物 1

HCID 731845934-[1-(hydroxy)-4,4-dimethyl-2-octenyl]hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

The crude racemic (3aR,4S,5R,6aS)-[S*,R*(E)]-rac-4-(4,4-Dimethyl-1-oxo-2-octenyl)hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one (12.9 g, 0.044 mole) in THF (60 mL) solution was cooled to -77° and treated dropwise with a 1M solution of potassium tri-sec-butylborohydride in THF (Aldrich "K-Selectride") ) (56 mL, 0.056 mole). Stirring at -77° was continued for 11/2 hours after the addition was completed. An aqueous solution of 10% NaOH (30 mL) was then added and the mixture allowed to warm to -20°. Aqueous 30% H2O2 (30 mL) was then added dropwise while keeping the temperature in the -5° to +5° range. After 1 hour, the cooling bath was removed and 3N HCL (90 mL) was added. Following 2 hours more of stirring, most of the solvent was stripped off and the product was taken up in ethyl acetate (200 mL). This solution was washed with aqueous NaHCO3, brine, and dried over Na2SO4. The volume was reduced to 100 mL by evaporation and this solution of crude [3aR-[3a alpha,4alpha-(1S*,2E),5beta,6a alpha]]-4-[1-(hydroxy)-4,4-dimethyl-2-octenyl]hexahydro-5-methyl-2H-cyclopenta[b]furan-2-one was used directly in Example VII.

後処理

  1. custom2 hours
  2. additionafter the addition
  3. temperatureto warm to -20°
  4. customin the -5° to +5° range
  5. customthe cooling bath was removed
  6. addition3N HCL (90 mL) was added
  7. waitFollowing 2 hours
  8. stirringmore of stirring, most of the solvent
  9. washThis solution was washed with aqueous NaHCO3, brine
  10. dry with materialdried over Na2SO4
  11. customThe volume was reduced to 100 mL by evaporation

出典と根拠

ORDレコード
ord-337839fbe9534431987b6341e0c9e582
出典データセット
uspto-grants-1987_11
特許番号
US04707555

関連ノート

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