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Sulfuric Acid → 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylhex-5-en-3-one

HRID 1003152
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HRID 1003152 반응식
[Cr](O)(O)(=O)=O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O.[CH3:22][C:23]1[O:28][CH2:27][N:26]([C:29]([CH3:36])([CH:31]([OH:35])[CH2:32][CH:33]=[CH2:34])[CH3:30])[C:25](=[O:37])[C:24]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>O.CCOCC>[CH3:22][C:23]1[O:28][CH2:27][N:26]([C:29]([CH3:30])([C:31](=[O:35])[CH2:32][CH:33]=[CH2:34])[CH3:36])[C:25](=[O:37])[C:24]=1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1
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참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 24425Chromic AcidHCID 25408Sodium DichromateHCID 22118283HCID 22118283, 화합물

생성물 1

HCID 187955282-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylhex-5-en-3-one수율 12.1%

시약·촉매·용매 2

HCID 962
Water
용매
2회
HCID 3283Diethyl Ether용매

실험 절차

Chromic acid [1.7 ml of a solution prepared by the addition of a solution of sodium dichromate (0.4 g) in water (1.2 ml) to concentrated sulphuric acid (0.54 ml) and diluted to 2 ml with water] was added dropwise at 25° C. to a stirred solution of 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylhex-5-ene-3-ol (1.0 g) in ether. After 18 hours the ether layer was separated, washed with sodium bicarbonate solution (2N) and with brine, dried (magnesium sulphate) and evaporated. The residue was purified by dry column chromatography on silica gel eluting with dichloromethane, to give 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylhex-5-en-3-one (Compound 7, 0.12 g) as a yellow oil, NMR 1H δ1.4(s,6H), 1.88(s,3H), 3.22(d,2H), 5.05(m,2H), 5.22(s,2H), 5.9(m.1H), 7.2-7.35(m,5H).

후처리

  1. customAfter 18 hours the ether layer was separated
  2. washwashed with sodium bicarbonate solution (2N) and with brine
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated
  5. customThe residue was purified
  6. dry with materialby dry column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-cab4c3cf42fa43b1aa8b6df939a31d21
출처 데이터셋
uspto-grants-2000_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06046135

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