Boron trifluoride etherate → HCID 20775668, compound

HRID 1815999Notes

Reaction equation

HRID 1815999 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[N:4]=[C:5]([CH:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]CC3C=CC=CC=3)=[CH:17][CH:16]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[S:6][CH:7]=1.B(F)(F)F.CCOCC>CCS>[F:30][C:2]([F:1])([F:29])[C:3]1[N:4]=[C:5]([CH:8]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=2)[CH2:9][C:10]([O:12][CH3:13])=[O:11])[S:6][CH:7]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherate2×HCID 20775667HCID 20775667, compound

Product 1

HCID 20775668HCID 20775668, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6343EthanethiolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl (±)-3[4-(trifluoromethyl)thiazol-2-yl]-4-(4-benzyloxyphenyl)butanoate (0.44 mmole, crude) in EtSH (5 mL) at RT was added BF3.OEt2 (0.3 mL). After 18 hr. additional BF3.OEt2 (0.3 mL) was added. After another 18 hr, the mixture was cooled to 0° C. and carefully quenched with saturated NaHCO3. The resulting mixture was extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was chromatographed on silica gel (30% EtOAc/hexanes) to give the title compound (123 mg, 81% over 3 steps) as a yellow oil: MS (ES) m/e 346 (M+H)+.

Workup

  1. waitAfter another 18 hr
  2. customcarefully quenched with saturated NaHCO3
  3. extractionThe resulting mixture was extracted with CH2Cl2 (3×25 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c470b17077b143e69db757e8f3feb91e
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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