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

HRID 1447532

반응식

HRID 1447532 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+].P([O-])([O-])([O-])=[O:21].[K+].[K+].[K+].CCOCC>CO.[Cl-].[Cl-].[Ti+2]>[CH3:1][CH:2]([C:8](=[O:21])[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 62657Potassium Phosphate, TribasicHCID 10942334Sodium MethoxideHCID 23341447Methyl 3,7-dimethyl-4-nitro-6-octenoate

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 monobasicsodium 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%). ir (neat) 1705 and 1735 cm-1 ; nmr (CDCl3) δ: ##STR9##

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-ccbde52221264cad9c866855ee631cf4
출처 데이터셋
uspto-grants-1979_12
특허 번호
US04177194

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