1-Iodo-2,3,4-trimethoxybenzene → HCID 10384873, 화합물

HRID 1453994노트

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HRID 1453994 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH3:13].C([Li])CCC.[Cl:19][CH:20]1[C:29](=O)[C:28]2[C:23](=[CH:24][C:25]([N:31]([CH3:33])[CH3:32])=[CH:26][CH:27]=2)[O:22][CH2:21]1>C1COCC1>[Cl:19][C:20]1[CH2:21][O:22][C:23]2[C:28]([C:29]=1[C:7]1[CH:6]=[C:5]([O:8][CH3:9])[C:4]([O:10][CH3:11])=[C:3]([O:12][CH3:13])[CH:2]=1)=[CH:27][CH:26]=[C:25]([N:31]([CH3:33])[CH3:32])[CH:24]=2

참가 물질

5

반응물 3

HCID 2569311-Iodo-2,3,4-trimethoxybenzeneHCID 57528878HCID 57528878, 화합물HCID 178418339Butyllithium

생성물 1

HCID 10384873HCID 10384873, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

Iodotrimethoxybenzene (40 mg, 0.133 mmol) was dissolved into 1 mL of dry THF and cooled to −78° C. The butyl lithium solution 1.16 M (126 μL, 0.146 mmol, 1.1 eq.) was added dropwise and the mixture was stirred at −78° C. for 15 min. 3-Chloro-7-dimethylamino-chroman-4-one (30 mg, 0.133 mmol) in 1 mL of dry THF was added and the mixture was allowed to warn to room temperature. After 3 h, the mixture was quenched with a saturated aqueous solution of NH4Cl (10 mL) and extracted with EtOAc (2×10 mL). Combined organic extracts were dried with Na2SO4 and concentrated. The residue was diluted in a mixture of 2 mL of ethanol and 0.75 mL of concentrated hydrochloric acid, and stirred overnight at room temperature. A saturated solution of sodium bicarbonate was added until neutralization and the resulting solution was extracted with EtOAc (2×25 mL).

후처리

  1. customto warn to room temperature
  2. waitAfter 3 h
  3. customthe mixture was quenched with a saturated aqueous solution of NH4Cl (10 mL)
  4. extractionextracted with EtOAc (2×10 mL)
  5. dry with materialCombined organic extracts were dried with Na2SO4
  6. concentrationconcentrated
  7. additionThe residue was diluted in a mixture of 2 mL of ethanol and 0.75 mL of concentrated hydrochloric acid
  8. stirringstirred overnight at room temperature
  9. additionA saturated solution of sodium bicarbonate was added until neutralization
  10. extractionthe resulting solution was extracted with EtOAc (2×25 mL)

출처 및 근거

ORD 기록
ord-c1601b41749a4055a28229d83905c1be
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476741B2

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