Potassium Phosphate, Tribasic → Methyl 6-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]hexanoate

HRID 1181590ノート

反応式

HRID 1181590 の反応式
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].C12BC(CCC1)CCC2.O1CCCC1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C@H:31]([O:33][CH2:34][C@H:35]1[CH2:37][O:36]1)[CH3:32].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.ClCCl.O1CCCC1>[O:36]1[CH2:37][C@@H:35]1[CH2:34][O:33][C@@H:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:8][CH3:9])=[O:7])[CH3:32]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 520082Methyl 5-HexenoateHCID 58981243(2R)-2-[[(1R)-1-(2-bromophenyl)ethoxy]methyl]oxiraneHCID 178419114HCID 178419114、化合物

生成物 1

HCID 58662604Methyl 6-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]hexanoate収率 49.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To methyl 5-hexenoate (608 mg) was added 0.5 M 9-bora bicyclo[3.3.1]nonane-tetrahydrofuran solution (9.5 ml) under ice-cooling and the mixture was stirred overnight at room temperature. The reaction mixture was added dropwise to a suspension of tetrahydrofuran (10 ml), (2R)-2-[[(1R)-1-(2-bromophenyl)ethoxy]methyl]oxirane (1.06 g) obtained in Example 1, Step 1, tri-potassium phosphate (1.32 g), [bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (170 mg) and the mixture was heated under reflux for 7 hr. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1) to give the title compound (621 mg).

後処理

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 7 hr
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:1)

出典と根拠

ORDレコード
ord-ea31a43bbcec4246a108e9f0af8137d4
出典データセット
uspto-grants-2007_10
特許番号
US07285572B2

反応ノート

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