p-Toluenesulfonyl azide → (1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

HRID 349263

반응식

HRID 349263 반응식
[H-].[Na+].[CH3:3][O:4][P:5]([CH2:9][C:10](=[O:12])[CH3:11])(=[O:8])[O:6][CH3:7].S([N:23]=[N+:24]=[N-])(C1C=CC(C)=CC=1)(=O)=O>C1C=CC=CC=1.O1CCCC1>[CH3:3][O:4][P:5]([C:9](=[N+:23]=[N-:24])[C:10](=[O:12])[CH3:11])(=[O:8])[O:6][CH3:7]

참가 물질

6

반응물 3

HCID 13661p-Toluenesulfonyl azideHCID 24758Sodium hydrideHCID 77872Dimethyl (2-oxopropyl)phosphonate

생성물 1

HCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one수율 92.3%

시약·촉매·용매 2

HCID 241Benzene용매3회HCID 8028Tetrahydrofuran용매

실험 절차

To sodium hydride (188 mg of a 60% solution in mineral oil, 113 mg clean, 4.70 mmol) in 14 mL of benzene and 2.5 mL of tetrahydrofuran, add (2-oxo-propyl)-phosphonic acid dimethyl ester (743 mg, 618 μL, 4.48 mmol) as a solution in 5 mL of benzene at 0° C. dropwise. The mix remains white and produces some gas. After 1 h at 0° C., add tosyl azide (940 mg, 4.70 mmol) as a solution in 2.5 mL of benzene and warm the mixture to RT. After 2.3 hours, pour the mix through a plug of Celite® rinsing with tetrahydrofuran, benzene, and ether. Concentrate the filtrate and purify the residue by chromatography (Hexanes/EtOAc gradient) to provide 794 mg of (1-Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester as a yellow solid. This material may be used directly. Exact Mass 192.03: mass spectrum (aspci): m/z=165.0 (M+1 (—N2).

후처리

  1. customproduces some gas
  2. waitAfter 2.3 hours
  3. additionpour the
  4. additionmix through a plug of Celite®
  5. washrinsing with tetrahydrofuran, benzene, and ether
  6. concentrationConcentrate the filtrate
  7. custompurify the residue by chromatography (Hexanes/EtOAc gradient)

출처 및 근거

ORD 기록
ord-448579858ec84eaab26152e38ed1daae
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179804B2

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