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

HRID 731021ノート

反応式

HRID 731021 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-c3d04a554bf74fc4b58f8453741186c0
出典データセット
uspto-grants-2009_09
特許番号
US07582781B2

反応ノート

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