Dimethylformamide → HCID 131723013, compound

HRID 2269305Notes

Reaction equation

HRID 2269305 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C@@H:13](OC)[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=1.C([Li])CCC.CN([CH:33]=[O:34])C.C1C[O:38][CH2:37]C1>C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C@@H:15]([C:16]1[CH:17]=[CH:18][C:19]([CH:33]=[O:34])=[CH:20][CH:21]=1)[O:38][CH3:37]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 54360741HCID 54360741, compoundHCID 178418339Butyllithium

Product 1

HCID 131723013HCID 131723013, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

(S)-4-[3-(5-Methyl-2-phenyl-4-oxazolyl)-3-methoxypropyl]bromobenzene (1.1 g, 2.8 mmol, prepared as described in Example 15) was dissolved in THF (30 mL), cooled to −78° C. and treated with n-butyllithium (2.5 M in THF, 1.2 mL, 3.0 mmol) dropwise via syringe. Following addition, the reaction mixture was stirred at −78° C. for an additional hour and treated with dry DMF (220 mg, 30 mmol). The reaction mixture was stirred at −78° C. for 90 minutes and at ambient temperature for 24 hours. The reaction mixture was diluted with ethyl acetate (200 mL), washed with water (50 mL), 10% aqueous hydrochloric acid (50 mL), water (50 mL), brine (50 mL) and dried (MgSO4). The solvent was removed in vacuo and the residue was purified on silica gel, eluting with hexane/ethyl acetate (3/1), to afford a viscous oil (580 mg, 62%). 1HNMR (300 MHz, CDCl3): δ2.0 (m, 2H), 2.3 (s, 3H), 2.5 (t, 2H), 3.2 (s, 3H), 4.15 (dd, 1H), 7.3 (m, 3H), 7.4 (d, 2H), 7.8 (d, 2H), 7.9 (m, 2H), 9.9 (s, 1H).

Workup

  1. additionaddition
  2. stirringThe reaction mixture was stirred at −78° C. for 90 minutes and at ambient temperature for 24 hours
  3. washwashed with water (50 mL), 10% aqueous hydrochloric acid (50 mL), water (50 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified on silica gel
  7. washeluting with hexane/ethyl acetate (3/1)

Sources & evidence

ORD record
ord-90bf9308f5a341cdb622b4e995d10493
Source dataset
uspto-grants-2001_12
Patent number
US06329408B1

Reaction notes

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