Methylenecyclobutane → Ethyl 5-oxa-6-azaspiro[3.4]oct-6-ene-7-carboxylate

HRID 1185940

반응식

HRID 1185940 반응식
[CH2:1]=[C:2]1[CH2:5][CH2:4][CH2:3]1.Cl/[C:7](=[N:13]\[OH:14])/[C:8]([O:10][CH2:11][CH3:12])=[O:9].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:11]([O:10][C:8]([C:7]1[CH2:1][C:2]2([CH2:5][CH2:4][CH2:3]2)[O:14][N:13]=1)=[O:9])[CH3:12]

참가 물질

5

반응물 3

HCID 14262MethylenecyclobutaneHCID 516892Sodium Bicarbonate2회HCID 95760052-Chloro-2-hydroxyiminoacetic acid ethyl ester2회

생성물 1

HCID 59611573Ethyl 5-oxa-6-azaspiro[3.4]oct-6-ene-7-carboxylate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

To a solution of methylenecyclobutane (2 mL, 21.6 mmol) in ethyl acetate (125 mL) was added (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (6.55 g, 43.2 mmol) and solid sodium bicarbonate (16.3 g, 194 mmol). The reaction mixture was sealed and stirred at room temperature for 6 hours. More (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (4 g, 26.4 mmol) and sodium bicarbonate (8 g, 95.2 mmol) were added and the reaction was stirred at room temperature for an additional 12 hours. The reaction was diluted with ethyl acetate and washed successively with water and brine, dried (MgSO4) and concentrated to yield crude 5-oxa-6-aza-spiro[3.4]oct-6-ene-7-carboxylic acid ethyl ester, contaminated with (Z)-Ethyl 2-chloro-2-(hydroxyimino)acetate and related compounds.

후처리

  1. customThe reaction mixture was sealed
  2. stirringthe reaction was stirred at room temperature for an additional 12 hours
  3. washwashed successively with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3a7590bf29734f35b508cbd37b5ce640
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08669234B2

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