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

HRID 1875

反応式

HRID 1875 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-60ba32da8a3a420db576adcfd7bcef8c
出典データセット
uspto-grants-1998_03
特許番号
US05726182

関連ノート

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