Hydrochloric Acid → 1,2-Epoxy-2-(2,5-difluorophenyl)butan-3-ol

HRID 731021노트

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HRID 731021 반응식
Cl[CH2:2][C:3]([C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])([OH:13])[CH:4]([O:6]C(=O)C(C)(C)C)[CH3:5].C[O-].[Na+].Cl>C1COCC1.CO>[O:13]1[C:3]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])([CH:4]([OH:6])[CH3:5])[CH2:2]1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 231170421-Chloro-2-(2,5-difluorophenyl)-3-pivaloyloxybutan-2-ol

생성물 1

HCID 230742631,2-Epoxy-2-(2,5-difluorophenyl)butan-3-ol수율 79%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1.70 g (5.3 mmol) of 1-chloro-2-(2,5-difluorophenyl)-3-(pivaloyloxy)butan-2-ol ((2S,3R)/(2R,3R)=94/6) in 20 mL of THF was cooled to 0° C., and 3.5 g (17.8 mmol) of a 28% solution of NaOMe in methanol was added thereto. The reaction was performed for 5 hours, and 20 mL of 1 M hydrochloric acid was added to stop the reaction. Then, extraction was performed with ethylacetate (30 mL). After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain 1.51 g of a crude product. The resulting product was purified by column on silica gel to obtain 0.838 g of the title compound (yield: 79%) ((2R,3R)/(2S,3R)=98/2 (the diastereomeric ratio was measured by HPLC under the same HPLC measurement conditions as those in Example 10, (2R,3R) 32 minutes, (2S,3R) 30 minutes). 1H-NMR (400 MHz, CDCl3) (2R,3R) δ: 1.70 (d, 3H, J=6.6 Hz), 2.80 (d, 1H, J=5.1 Hz), 3.34 (d, 1H, J=5.1 Hz), 4.17 (q, 1H, 6.6 Hz), 6.98-7.00 (m, 2H), 7.14-7.26 (m, 1H)

후처리

  1. customthe reaction
  2. extractionThen, extraction
  3. dry with materialAfter drying over anhydrous sodium sulfate, concentration
  4. customto obtain 1.51 g of a crude product
  5. customThe resulting product was purified by column on silica gel

출처 및 근거

ORD 기록
ord-c3d04a554bf74fc4b58f8453741186c0
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582781B2

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