Ammonium Chloride → HCID 15521111, compound

HRID 1062652Notes

Reaction equation

HRID 1062652 reaction equation
[CH2:1]([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)[C:2]#[CH:3].[CH2:11]([Li])CCC.[Br:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1.[Cl-].[NH4+]>C1COCC1.CCCCCC>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:25])[C:11]#[C:3][CH2:2][CH2:1][O:4][CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][O:6]2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 756094-Bromophenyl isocyanateHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 178418339Butyllithium

Product 1

HCID 15521111HCID 15521111, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 4.98 g (35.5 mmol) of tetrahydro-2-(2-propynyloxy)-2H-pyran in 70 mL of THF under N2 was added 14.2 mL (35.5 mmol) of 2.5 M n-butyllithium in hexane. After 15 minutes, 7.03 g (35.5 mmol) of 4-bromophenylisocyanate was added and then the reaction was allowed to warm to room temperature. Saturated aqueous ammonium chloride (20 mL) was added and the mixture extracted with 30 mL ethyl acetate three times. The combined organic extracts were dried with MgSO4, concentrated to an oil in vacuo and then chromatographed on silica with 20% EtOAc/hexane to give 7.1 g (59%) of the desired alkyne. 1H NMR (CDCl3) δ: 7.53 (br s, 1H); 7.43 (d, 2H); 7.42 (d, 2H); 4.80 (m, 1H); 4.43 (d, 1H); 4.40 (d, 1H); 3.83 (m, 1H); 3.59 (m, 1H); 1.7 (m, 6H).

Workup

  1. extractionthe mixture extracted with 30 mL ethyl acetate three times
  2. dry with materialThe combined organic extracts were dried with MgSO4
  3. concentrationconcentrated to an oil in vacuo
  4. customchromatographed on silica with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-b1ee649dac6e4282894c2fa2e3537578
Source dataset
uspto-grants-2005_11
Patent number
US06962935B2

Reaction notes

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