Water → HCID 70160899, compound

HRID 1018374

Reaction equation

HRID 1018374 reaction equation
[H-].[Na+].[Br-].[CH3:4][O:5][C:6]([C:8]1[CH:9]=[C:10]([CH:31]=[CH:32][CH:33]=1)[CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7].[C:34]12([CH2:44][CH2:45][C:46]3[N:50]([CH3:51])[C:49]([C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=4[CH3:58])=[N:48][C:47]=3[CH:59]=O)[CH2:43][CH:38]3[CH2:39][CH:40]([CH2:42][CH:36]([CH2:37]3)[CH2:35]1)[CH2:41]2.O>C1COCC1.C(OCC)(=O)C>[CH3:4][O:5][C:6](=[O:7])[C:8]1[CH:33]=[CH:32][CH:31]=[C:10]([CH:11]=[CH:59][C:47]2[N:48]=[C:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[CH3:58])[N:50]([CH3:51])[C:46]=2[CH2:45][CH2:44][C:34]23[CH2:43][CH:38]4[CH2:37][CH:36]([CH2:42][CH:40]([CH2:39]4)[CH2:41]2)[CH2:35]3)[CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10051285Phosphonium, [[3-(methoxycarbonyl)phenyl]methyl]triphenyl-, bromideHCID 184054185-(2-Adamantan-1-yl-ethyl)-1-methyl-2-o-tolyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 70160899HCID 70160899, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% dispersion in oil) (122 mg, 3.05 mmol) was added to an ice cooled suspension of 3-methoxycarbonyl-benzyl-triphenylphosphonium bromide (1.25 g, 2.54 mmol) in THF (5 ml). The yellow suspension was stirred at room temperature for 10 min, cooled to 0° C. and the solution of the product of step b (7686 mg, 2.12 mmol) in THF (5 ml) was added. The suspension was allowed to warm to room temperature and stirred for 72 h. Water (2 ml), then ethyl acetate (40 ml) were added. The organic phase was washed with water (30 ml), brine (30 ml), dried (MgSO4) and the solvent was evaporated. The crude product was purified by flash column chromatography (silica, hexane/ethyl acetate 5:2) to afford the product as 2:1 mixture of trans/cis isomers (778 mg, 74%).

Workup

  1. temperaturecooled
  2. temperaturecooled to 0° C.
  3. temperatureto warm to room temperature
  4. stirringstirred for 72 h
  5. washThe organic phase was washed with water (30 ml), brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated
  8. customThe crude product was purified by flash column chromatography (silica, hexane/ethyl acetate 5:2)
  9. customto afford the product
  10. additionas 2:1 mixture of trans/cis isomers (778 mg, 74%)

Sources & evidence

ORD record
ord-67e3a5df10fa4d52a1bf856fb10494f4
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Linked notes

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