1-Iodo-2,3,4-trimethoxybenzene → HCID 10384873、化合物

HRID 1453994ノート

反応式

HRID 1453994 の反応式
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

参加物

5

反応物 3

HCID 2569311-Iodo-2,3,4-trimethoxybenzeneHCID 57528878HCID 57528878、化合物HCID 178418339Butyllithium

生成物 1

HCID 10384873HCID 10384873、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-c1601b41749a4055a28229d83905c1be
出典データセット
uspto-grants-2009_01
特許番号
US07476741B2

反応ノート

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