Methanol → 4-t-Butoxy-2,3,6-trifluoro-5-methoxypyridine

HRID 1875

반응식

HRID 1875 반응식
[C:1]([O:5][C:6]1[C:11]([OH:12])=[C:10]([F:13])[N:9]=[C:8]([F:14])[C:7]=1[F:15])([CH3:4])([CH3:3])[CH3:2].[C:16]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]1[C:11]([O:12][CH3:16])=[C:10]([F:13])[N:9]=[C:8]([F:14])[C:7]=1[F:15])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 106565874-t-Butoxy-2,3,6-trifluoro-5-hydroxypyridine

생성물 1

HCID 104899104-t-Butoxy-2,3,6-trifluoro-5-methoxypyridine수율 85.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 237 mg (1.07 mmol) of 4-t-butoxy-2,3,6-trifluoro-5-hydroxypyridine, from step 275a above, in 3 mL of anhydrous THF was added 335 mg (1.277 mmol) of triphenyl phosphine and 0.060 mL (1.48 mmol) of methanol. To this solution was added 0.200 mL (1.270 mmol) of DEAD dropwise at room temperature. The reaction was complete in 10 min, so the solvents were removed under vacuum and the residue was purified by flash chromatography on silica gel, eluting with 1:16 ethyl acetate:hexane to give 215.6 mg of the title product as a colorless liquid after removal of the solvent.

후처리

  1. customwere removed under vacuum
  2. customthe residue was purified by flash chromatography on silica gel
  3. washeluting with 1:16 ethyl acetate

출처 및 근거

ORD 기록
ord-60ba32da8a3a420db576adcfd7bcef8c
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726182

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