Benzoyl chloride → 1,3-Benzodioxole-5-acetic acid, 6-benzoyl-, methyl ester

HRID 442657노트

반응식

HRID 442657 반응식
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=2[O:2]1.Cl[Sn](Cl)(Cl)Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCCCCC.CCOC(C)=O>[C:20]([C:6]1[CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]2=[CH:4][C:5]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

7

반응물 4

HCID 7412Benzoyl chlorideHCID 24287Tin tetrachlorideHCID 266588Methyl 2-(1,3-dioxaindan-5-yl)acetateHCID 516892Sodium Bicarbonate

생성물 1

HCID 4069581,3-Benzodioxole-5-acetic acid, 6-benzoyl-, methyl ester수율 48%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21226206Ethyl acetate hexane용매

실험 절차

To a solution of methyl 3,4-methylenedioxyphenylacetate (150 mg, 0.77 mmol) in CH2Cl2 (5 mL) was added SnCl4 (1.0M solution in CH2Cl2 ; 1.5 mL, 1.5 mmol) at 0° C. Then benzoyl chloride (130 μL, 1.1 mmol) was added. The reaction mixture was allowed to warm slowly to room temperature. After 24 h, the mixture was added to a saturated NaHCO3 solution (30 mL), diluted with 1:1 hexane/EtOAc (60 mL), washed with water and brine, and dried over Na2SO4. The solvent was removed in vacuo and the resulting residue was separated by chromatography on silica gel (4:1 hexane/EtOAc) to yield the title compound (110 mg, 48%). 1H NMR (CDCl3) 7.78-7.45 (m, 5H), 6.88 (s, 1H), 6.84 (s, 1H), 6.04 (s, 2H), 3.80 (s, 2H), 3.61 (s, 3H).

후처리

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed in vacuo
  4. customthe resulting residue was separated by chromatography on silica gel (4:1 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-e441c82b165346df89d10a8470b72bed
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891871

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