Diethyl Ether → Methyl 3,7-dimethyl-4-oxo-6-octenoate

HRID 27648

반응식

HRID 27648 반응식
[CH3:1][CH:2]([CH:8]([N+]([O-])=O)[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH2:3][C:4]([O:6][CH3:7])=[O:5].C[O-].[Na+].[OH:20]P([O-])(O)=O.[K+].[OH-].[Na+].CCOCC>CO.[Cl-].[Cl-].[Ti+2]>[CH3:1][CH:2]([C:8](=[O:20])[CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12])[CH2:3][C:4]([O:6][CH3:7])=[O:5]

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 10942334Sodium MethoxideHCID 23341447Methyl 3,7-dimethyl-4-nitro-6-octenoateHCID 24942486NaOH KH2PO4

생성물 1

HCID 15340230Methyl 3,7-dimethyl-4-oxo-6-octenoate수율 35%

시약·촉매·용매 2

HCID 10290777Titanium(2+);dichloride촉매HCID 887Methanol용매2회

실험 절차

A solution of methyl 3,7-dimethyl-4-nitro-6-octenoate (24.55 g, 0.107 m) in methanol (10 ml) is added dropwise to a solution of sodium methoxide (6.37 g, 0.118 m) in methanol (250 ml) at room temperature under nitrogen. The mixture is stirred for 1 hour, added to a mixture of 20% titanous chloride (170 ml, 0.267 m) and pH 7 buffer (potassium phosphate monobasic-sodium hydroxide buffer) solution (340 ml). The resulting mixture is stirred for 30 minutes after which it is treated with ether (1 l). The organic phase is separated, dried (Na2SO4) and evaporated in vacuo to give the crude product (15.4 g). This material is purified by column chromatography on silica gel (300 g, 2% ethyl acetate in hexane) to give methyl 3,7-dimethyl-4-oxo-6-octenoate as a colorless liquid (6.8 g, 35%).

후처리

  1. stirringThe resulting mixture is stirred for 30 minutes after which it
  2. customThe organic phase is separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give the crude product (15.4 g)
  6. customThis material is purified by column chromatography on silica gel (300 g, 2% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-aa5477c2625d4b8b8d317708dc0a77ff
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04222937

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