Phenol → HCID 131719536, compound

HRID 741801Notes

Reaction equation

HRID 741801 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[Si:13]([O:30]CCC(C1C=CC=CC=1)=O)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:41]1(O)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[CH2:48]1C[O:51][CH2:50][CH2:49]1>>[OH:51][C:50]([C:41]1[CH:42]=[C:43]([O:30][Si:13]([C:26]([CH3:27])([CH3:29])[CH3:28])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:44]=[CH:45][CH:46]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[CH2:49][CH3:48]

Participants

6

Reactant 5

HCID 996PhenolHCID 79732-BromopyridineHCID 8028Tetrahydrofuran2×HCID 54215325HCID 54215325, compoundHCID 178418339Butyllithium

Product 1

HCID 131719536HCID 131719536, compoundYield 94%

Conditions

Temperature
0 °C

Procedure

n-BuLi (2.4M in hexane, 674 μL, 1.62 mmol) was added dropwise (15 min.) to 2-bromopyridine (147 μL, 1.54 mmol) in THF (5 mL) at -78° C. and under Ar. The solution was stirred for 40 min. at this temperature. The 3-(tert-butyldiphenylsilyloxy)propiophenone (499 mg, 1.28 mmol) from Phenol 8, Step 3 in THF (2 mL) was then added dropwise (10 min.). The mixture was kept at -78° C. for 30 min. and allowed to warm to 0° C. After 20 min. the reaction was quenched with a saturated NH4Cl solution and extracted with EtOAc (3×). The combined organics were washed with 25% NH4OAc buffer, H2O, brine, dried (MgSO4) and concentrated to give an off-white gum, that was purified by column chromatography on silica gel (EtOAc/hexane 1:9), affording the title compound as a colorless gum (563 mg, 94%).

Workup

  1. waitThe mixture was kept at -78° C. for 30 min.
  2. customAfter 20 min. the reaction was quenched with a saturated NH4Cl solution
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organics were washed with 25% NH4OAc buffer, H2O, brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give an off-white gum, that
  8. customwas purified by column chromatography on silica gel (EtOAc/hexane 1:9)

Sources & evidence

ORD record
ord-4c6ae848f9e44adb8ff8d7e383a721e2
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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