Methanol → HCID 86705533, compound

HRID 2279546Notes

Reaction equation

HRID 2279546 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:12]2[CH2:14][O:13]2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C[O-].[Na+].[OH2:18].[CH3:19]O>>[F:1][C:2]1[CH:3]=[C:4]([C@@H:12]([OH:18])[CH2:14][O:13][CH3:19])[CH:5]=[CH:6][C:7]=1[C:8]([F:9])([F:10])[F:11]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 10942334Sodium MethoxideHCID 86705532HCID 86705532, compound

Product 1

HCID 86705533HCID 86705533, compoundYield 90.9%

Procedure

To a solution of 312 (0.600 g, 2.91 mmol) and MeOH (1 mL) was added NaOMe (11.6 mL, 5.82 mmol) in MeOH and the reaction was stirred at RT for 3 d, then poured into water and extracted with DCM. The combined organic extractions were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:10) to afford 0.630 g (90.9%) of (R)-1-(3-fluoro-4-(trifluoromethyl)phenyl)-2-methoxyethanol (314) which was contaminated with a small amount of the regioisomeric epoxide ring-opening product.

Workup

  1. extractionextracted with DCM
  2. extractionThe combined organic extractions
  3. dry with materialwere dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with DCM/MeOH (500:10)

Sources & evidence

ORD record
ord-4c115e002865495ea935332cb50a4319
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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