Diethyl Ether → HCID 58227420, compound

HRID 2092972Notes

Reaction equation

HRID 2092972 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[S:10][C:11]([CH:14]=[O:15])=[CH:12][N:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCOCC>C1COCC1>[C:16]1([CH:14]([C:11]2[S:10][C:9]([C:8]#[C:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:13][CH:12]=2)[OH:15])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 58227416HCID 58227416, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 58227420HCID 58227420, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-phenylethynyl-thiazole-5-carbaldehyde (Example 205, 197 mg, 0.924 mmol) in THF (5.0 mL) was cooled at 0° C. and treated with a 3.0 M solution of phenyl magnesium bromide in Ether (340 μL, 1.0 mmol). After stirring for about 30 minutes at 0° C., the reaction was quenched with saturated aqueous ammonium chloride (25 mL), diluted with EtOAc (25 mL), transferred to a 125-mL separatory funnel and extracted. The layers were separated and the aqueous layer was extracted again with EtOAc (25 mL). The combined organic layers were then washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative TLC, eluting with 25% EtOAc in hexanes to afford the titled compound, pPhenyl-(2-phenylethynyl-thiazol-5-yl)-methanol (190 mg, 71%), as a pale yellow oil.

Workup

  1. customthe reaction was quenched with saturated aqueous ammonium chloride (25 mL)
  2. additiondiluted with EtOAc (25 mL)
  3. customtransferred to a 125-mL separatory funnel
  4. extractionextracted
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted again with EtOAc (25 mL)
  7. washThe combined organic layers were then washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by preparative TLC
  12. washeluting with 25% EtOAc in hexanes

Sources & evidence

ORD record
ord-803c1ecb87844b8d865bb6867fd7a45a
Source dataset
uspto-grants-2013_05
Patent number
US08440837B2

Reaction notes

Loading…