Sodium Hydroxide → (2S)-l-Benzyloxymethoxy-2,6-dimethyl-5,6-epoxy-heptane

HRID 493062ノート

反応式

HRID 493062 の反応式
[CH2:1]([O:8][CH2:9][O:10][CH2:11][C@@H:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=[O:21].[Na+].ClC1C=C(C=CC=1)C(OO)=O.[OH-].[Na+]>C(Cl)Cl.CCOCC.O>[CH2:1]([O:8][CH2:9][O:10][CH2:11][C@@H:12]([CH3:19])[CH2:13][CH2:14][CH:15]1[O:21][C:16]1([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57680469(S)-1-Benzyloxymethoxy-2,6-d imethyl-hept-5-ene

生成物 1

HCID 57680482(2S)-l-Benzyloxymethoxy-2,6-dimethyl-5,6-epoxy-heptane収率 74%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

Olefin 5 (3.2 g, 12.2 mmol) was dissolved in anhydrous CH2Cl2 (60 mL), and NaHCO3 (1.6 g, 18.4 mmol) was added. Then, 3-chloroperoxybenzoic acid (60%, 12.8 g, 36.6 mmol) was added at room temperature with stirring. The stirring was continued for 24 hours, and the mixture was diluted with ether, and shaken with water and 2M NaOH. The organic layer was washed with water and saturated NH4Cl, dried over Na2SO4, and evaporated. The residue was chromatographed on silica gel using hexane/EtOAc (9:1) as an eluent to give the oily product 6 (2.5 g, 74%).

後処理

  1. washThe organic layer was washed with water and saturated NH4Cl
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-a64153ac96ab4427b119a33b1e7c0f48
出典データセット
uspto-grants-2009_05
特許番号
US07534777B2

反応ノート

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