Water → (2S,3R)-1,2-Epoxy-2-(2,4-difluorophenyl)butan-3-ol

HRID 731018Notes

Reaction equation

HRID 731018 reaction equation
Cl[CH2:2][C@:3]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([OH:7])[C@H:4]([OH:6])[CH3:5].C[O-].[Na+].O>CO>[O:7]1[C@:3]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])([C@H:4]([OH:6])[CH3:5])[CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 67175587(2R,3R)-1-Chloro-2-(2,4-difluorophenyl)butane-2,3-diol

Product 1

HCID 10867332(2S,3R)-1,2-Epoxy-2-(2,4-difluorophenyl)butan-3-olYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 1.00 g (4.23 mmol) of (2R,3R)-1-chloro-2-(2,4-difluorophenyl)butane-2,3-diol in 8 mL of methanol was cooled in ice, and 0.91 g (4.65 mmol) of a 28% solution of NaOMe in methanol was added thereto. The reaction was performed for 2 hours, and 10 mL of water was added to stop the reaction. Then, extraction was performed with 20 mL of ethyl acetate. After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain a crude product. The product was quantitatively analyzed by HPLC (under the same HPLC measurement conditions as those in Example 10). The title compound was obtained in a yield of 97%. 1H-NMR (400 MHz, CDCl3) δ: 1.19 (d, 3H, J=6.3 Hz), 2.22 (s, 1H), 2.91 (d, 1H, J=4.9 Hz), 3.28 (d, 1H, J=4.9 Hz), 4.11 (d, 1H, J=6.3 Hz), 6.80-6.91 (m, 2H), 7.34-7.39 (m, 1H).

Workup

  1. customthe reaction
  2. extractionThen, extraction
  3. dry with materialAfter drying over anhydrous sodium sulfate, concentration
  4. customto obtain a crude product

Sources & evidence

ORD record
ord-271b56d281184035ade6144bb96207f2
Source dataset
uspto-grants-2009_09
Patent number
US07582781B2

Reaction notes

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