Tetrahydrofuran → HCID 14026685, compound

HRID 1251568Notes

Reaction equation

HRID 1251568 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[CH3:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][N:18]=1.[Cl:23][C:24]1[CH:33]=[CH:32][C:27]([C:28](OC)=[O:29])=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:33]=[CH:32][C:27]([C:28](=[O:29])[CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][N:18]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 14307Methyl 4-chlorobenzoateHCID 189224-MethylpyrimidineHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 14026685HCID 14026685, compound

Procedure

Lithium bis(trimethylsilyl)amide 1.0 M in THF (4.25 L, 4.25 mol) was cooled to −70° C. with stirring under nitrogen. 4-methylpyrimidine (250 g, 2.66 mol) was added followed by Methyl 4-chlorobenzoate (453.2 g, 2.66 mol). The cooling bath was removed and the mixture was allowed to warm to room temperature and stir for 16 h. Water (3 L) and ethyl acetate (3 L) were added followed by acetic acid (200 mL). The layers were separated and the organic layer was washed with brine and dried over magnesium sulfate. The mixture was then concentrated to 800 mL and hexanes (250 mL) were added. The product was filtered, washed with hexanes, and air dried to provide a yellow solid. (388.1 g, 64%): mp 110.4-110.5° C. 1H NMR (acetone-d6/300 MHz) 14.9 (bs, 1H), 8.8 (s, 1H), 8.4 (m, 1H), 7.7 (d, 2H, J=8.7 Hz), 7.3 (d, 2H, J=8.7 Hz), 6.9 (m, 1H), 5.9 (s, 1H).

Workup

  1. customThe cooling bath was removed
  2. stirringstir for 16 h
  3. additionWater (3 L) and ethyl acetate (3 L) were added
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe mixture was then concentrated to 800 mL and hexanes (250 mL)
  8. additionwere added
  9. filtrationThe product was filtered
  10. washwashed with hexanes, and air
  11. customdried
  12. customto provide a yellow solid

Sources & evidence

ORD record
ord-faf388dc8f7f43879520313739f358d8
Source dataset
uspto-grants-2002_01
Patent number
US06342608B1

Reaction notes

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