HCID 57691462, compound → HCID 76594467, compound

HRID 1867637Notes

Reaction equation

HRID 1867637 reaction equation
[CH2:1]([Li])[CH2:2]CC.[O:6]1[CH2:11][CH2:10][CH2:9][O:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=O)[CH2:19][O:20][CH2:21][C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=1>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1>[F:29][C:28]([F:31])([F:30])[C:26]1[CH:27]=[C:22]([CH:23]=[C:24]([C:32]([F:35])([F:33])[F:34])[CH:25]=1)[CH2:21][O:20][CH2:19][C:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH:7]1[O:8][CH2:9][CH2:10][CH2:11][O:6]1)=[CH:1][CH3:2]

Participants

5

Reactant 2

HCID 57691462HCID 57691462, compoundHCID 178418339Butyllithium

Product 1

HCID 76594467HCID 76594467, compound

Reagents, catalysts & solvents 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of ethyl triphenylphosphonium bromide (7.62 g, 20.5 mmol) in tetrahydrofuran (40 mL) at −78° C. was added n-butyllithium (1.6 M in hexane, 12.8 mL, 20.5 mmol). The resulting suspension was warmed to 0° C., stirred 30 min, and cooled to −78° C. The reaction was treated with 1-(2-(1,3-dioxan-2-yl)phenyl)-2-(3,5-bis(trifluoromethyl)benzyloxy)ethanone (2.80 g, 6.25 mmol) as a solid. The reaction was placed in a 0° C. bath and stirred for 30 min. The reaction was stirred at room temperature for 1 h, and quenched by addition of saturated ammonium chloride. The mixture was extracted with ether, which was washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. The reaction was purified by flash chromatography (5-->20% EtOAc/Hex) to give 1.78 g (62%). Mass spec.: 483.13 (MNa)+.

Workup

  1. temperaturecooled to −78° C
  2. customwas placed in a 0° C.
  3. stirringstirred for 30 min
  4. stirringThe reaction was stirred at room temperature for 1 h
  5. customquenched by addition of saturated ammonium chloride
  6. extractionThe mixture was extracted with ether, which
  7. washwas washed with water (2×)
  8. dry with materialbrine, dried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe reaction was purified by flash chromatography (5-->20% EtOAc/Hex)
  11. customto give 1.78 g (62%)

Sources & evidence

ORD record
ord-3c776edf0ad24047a750b2023d2a01b7
Source dataset
uspto-grants-2009_12
Patent number
US07632861B2

Reaction notes

Loading…