Tetrahydrofuran → HCID 21469519, compound

HRID 1938682Notes

Reaction equation

HRID 1938682 reaction equation
C1COCC1.[C:6]1([CH:12]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:13]2[N:14]=[N:15][N:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[N:17]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Li]CCCC.[CH:41]([C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH:50]([CH3:52])[CH3:51])[C:45]=1[N:53]=[C:54]=[O:55])([CH3:43])[CH3:42]>O>[CH3:43][CH:41]([C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH:50]([CH3:51])[CH3:52])[C:45]=1[NH:53][C:54](=[O:55])[C:12]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:13]1[N:14]=[N:15][N:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[N:17]=1)[CH3:42]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 922592,6-Diisopropylphenyl isocyanateHCID 21469516HCID 21469516, compoundHCID 178418339Butyllithium

Product 1

HCID 21469519HCID 21469519, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a THF solution (30 mL) of 5-(diphenylmethyl)-2-dodecyl-2H-tetrazole (1.0 g, 0.0025 mol) at -30° C. under a nitrogen atmosphere with stirring was added n-BuLi (1.62 mL, 1.6M in hexanes, 0.0026 mol). The resulting deep-red solution was stirred for 30 minutes before a THF solution (10 mL) of 2,6-diisopropyl-phenylisocyanate (0.53 mL, 0.0024 mol) was added dropwise over 10 minutes. The resulting yellow solution was allowed to warm to room temperature over 24 hours. Water (10 mL) was then added and the solution partitioned between ethyl acetate and water. The organic extract was washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo to yield a yellow oil which was flash chromatographed (5% EtOAc-Hex as eluant, SiO2) to yield 1.16 g of the title product as a clear oil.

Workup

  1. additionwas added dropwise over 10 minutes
  2. customthe solution partitioned between ethyl acetate and water
  3. extractionThe organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield a yellow oil which
  9. customchromatographed (5% EtOAc-Hex as eluant, SiO2)

Sources & evidence

ORD record
ord-90eff0053b3f4b2ab249cc9604f79590
Source dataset
uspto-grants-1997_12
Patent number
US05693657

Reaction notes

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