Tetrahydrofuran → HCID 86606922, compound

HRID 747028Notes

Reaction equation

HRID 747028 reaction equation
[CH2:1]([Mg]Br)[CH:2]=[CH2:3].[F:6][C:7]([F:38])([F:37])[C:8]1[CH:9]=[C:10]([C@H:18]([O:20][C@@H:21]2[C@@H:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:25]([C:33](OC)=[O:34])[CH2:24][CH2:23][O:22]2)[CH3:19])[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1.[Cl-].[NH4+].O1C[CH2:44][CH2:43][CH2:42]1>>[CH2:1]([C:33]([CH2:44][CH:43]=[CH2:42])([C@@H:25]1[CH2:24][CH2:23][O:22][C@H:21]([O:20][C@@H:18]([C:10]2[CH:11]=[C:12]([C:14]([F:17])([F:15])[F:16])[CH:13]=[C:8]([C:7]([F:6])([F:38])[F:37])[CH:9]=2)[CH3:19])[C@H:26]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[OH:34])[CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 86606920HCID 86606920, compoundHCID 178455850HCID 178455850, compound

Product 1

HCID 86606922HCID 86606922, compoundYield 95%

Procedure

Allylmagnesium bromide (1.0M in hexanes, 8.8 mL, 8.8 mmol) was added slowly to a stirred, cooled (0° C.) solution of methyl(2R,3R,4R)-2-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}tetrahydro-3-phenyl-2H-pyran-4-carboxylate (Description 37; 1.4 g, 2.9 mmol) in tetrahydrofuran (10 mL). The mixture was warmed to room temperature and stirred for 30 minutes. Saturated aqueous ammonium chloride (50 mL) was added and the mixture was extracted with ethyl acetate (3×30 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced-pressure. The residue was purified by column chromatography on silica gel, eluting with EtOAc/hexane (80:20), to give the title compound as a colorless oil (1.48 g, 95%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×30 mL)
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. customthe solvent was evaporated under reduced-pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with EtOAc/hexane (80:20)

Sources & evidence

ORD record
ord-cbe06e5f86ce4ca99a755ecc69de60af
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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