2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-(2-Chlorobenzoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 1170455노트

반응식

HRID 1170455 반응식
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([CH:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:9])=[O:15]

참가 물질

5

반응물 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 691102-Chlorobenzoyl chloride

생성물 1

HCID 167368235-(2-Chlorobenzoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione수율 50.9%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

A solution of 4-(dimethylamino)pyridine (33.96 g; 278 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (20.0 g, 139 mmol) in 50 mL of CH2Cl2 was cooled in an ice-salt bath to −10° C. A solution of 2-chlorobenzoyl chloride (29.2 g, 167 mmol) in 20 mL of CH2Cl2 was added dropwise via addition funnel over 1 h. After stirring cold for 1 h, the reaction was allowed to warm to rt and stirred for an additional 3 h. The resulting yellow-orange solution was then extracted with an aq. 10% HCl solution (200 mL) and 200 mL of brine. After drying with MgSO4, the mixture was filtered and the solvent was removed in vacuo. The resulting orange oil was triturated with hexanes (3×50 mL), affording the title compound (20 g) as a yellow solid.

후처리

  1. stirringstirred for an additional 3 h
  2. extractionThe resulting yellow-orange solution was then extracted with an aq. 10% HCl solution (200 mL) and 200 mL of brine
  3. dry with materialAfter drying with MgSO4
  4. filtrationthe mixture was filtered
  5. customthe solvent was removed in vacuo
  6. customThe resulting orange oil was triturated with hexanes (3×50 mL)

출처 및 근거

ORD 기록
ord-f28672abc23541b2a269a6ecaf150c30
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825278B2

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