Hydrochloric Acid → Methyl 6-chloro-2,2-dimethylchroman-8-carboxylate

HRID 402802노트

반응식

HRID 402802 반응식
[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=2)[O:3]1.Cl.C1C(=O)N([Cl:25])C(=O)C1.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[Na+]>ClCCl.CO.O>[Cl:25][C:7]1[CH:8]=[C:9]2[C:4](=[C:5]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=1)[O:3][C:2]([CH3:16])([CH3:1])[CH2:11][CH2:10]2

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 66765741Methyl 2,2-dimethylchroman-8-carboxylate

생성물 1

HCID 66765164Methyl 6-chloro-2,2-dimethylchroman-8-carboxylate

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
10 °C

실험 절차

To a solution of methyl 2,2-dimethyl-3,4-dihydro-2H-chromene-8-carboxylate (330 mg, 1.50 mmol) in dichloromethane (3.74 mL) and methanol (3.74 mL) was added concentrated HCl (61.5 μL, 0.75 mmol) at 10° C. NCS (206 mg, 1.54 mmol) as added portion-wise. The solution was stirred for 1 hour at 8-12° C. The solution was then poured into a mixture of water (5.00 mL), saturated aqueous sodium thiosulfate (5.00 mL), 1 N aqueous NaOH (5.00 mL) and dichloromethane (30.0 mL). The mixture was stirred for 15 minutes at room temperature and the two phases were separated. The organic phase was acidified to pH<2 with 1 N aqueous HCl. The mixture was then extracted with dichloromethane (10.0 mL, 2×). The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with 0-15% EtOAc/hexanes to give the desired product as a colorless oil.

후처리

  1. stirringThe mixture was stirred for 15 minutes at room temperature
  2. customthe two phases were separated
  3. extractionThe mixture was then extracted with dichloromethane (10.0 mL, 2×)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude residue was purified by silica gel chromatography
  8. washeluting with 0-15% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-a20f0fe3bbda415b8f40a4c89e217936
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742110B2

반응 노트

불러오는 중…