Sodium Iodide → Methyl 4-((di-tert-butoxyphosphoryloxy)methyl)benzoate

HRID 595040

반응식

HRID 595040 반응식
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[P:13]([O-:25])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[K+].[I-].[Na+]>CN(C=O)C.CCOCC>[C:21]([O:20][P:13]([O:25][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])([CH3:24])([CH3:23])[CH3:22]

참가 물질

6

반응물 3

HCID 5238Sodium IodideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 23674467Potassium di-tert-butyl phosphate

생성물 1

HCID 90087888Methyl 4-((di-tert-butoxyphosphoryloxy)methyl)benzoate

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

Methyl 4-(bromomethyl)benzoate (1200 mg, 5.24 mmol), potassium di-tert-butyl phosphate (1431 mg, 5.76 mmol) and sodium iodide (785 mg, 5.24 mmol) were combined in DMF (3.00 mL) under nitrogen. The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with ether, washed with 10% LiCl solution and brine, then dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane/EtOAc) to provide Preparation 55A (571 mg, 1.593 mmol, 30%): 1H NMR (400 MHz, CDCl3) δ 8.03 (d, J=8.4 Hz, 2H), 7.53-7.37 (m, 2H), 5.05 (d, J=7.5 Hz, 2H), 3.92 (s, 3H), 1.48 (d, J=0.4 Hz, 18H).

후처리

  1. washwashed with 10% LiCl solution and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (hexane/EtOAc)
  6. customto provide

출처 및 근거

ORD 기록
ord-ddb14697f5774d0e8ba27545822bb64b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242941B2

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