Ammonium Chloride → tert-Butyl 4-vinylnaphthalen-1-ylcarbamate

HRID 2069037Notes

Reaction equation

HRID 2069037 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH:7]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:11][CH:10]=1)=O.[NH4+].[Cl-]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH:7]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:11][CH:10]=1)=[CH2:1]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 58745967tert-Butyl 4-formylnaphthalen-1-ylcarbamate

Product 1

HCID 68313610tert-Butyl 4-vinylnaphthalen-1-ylcarbamateYield 72.1%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of methyltriphenylphosphonium bromide (3.82 g, 10.69 mmol) in THF (20 mL) at 0° C. under nitrogen was added potassium tert-butoxide (1.20 g, 10.69 mmol) and the reaction mixture was stirred at 0° C. for 15 min, then warmed to RT and stirred for a further 45 min. The suspension was cooled to 0° C. and a solution of tert-butyl 4-formylnaphthalen-1-ylcarbamate (30) (1.16 g, 4.28 mmol) in THF (10 mL) was added dropwise. The reaction mixture was warmed to RT and stirred for 2 hr. Saturated aqueous NH4Cl solution (30 mL) was added and the mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 0-10% ethyl acetate in isohexane, gradient elution) to afford the title compound (31) as a white solid (0.831 g, 72%): m/z 268 (m-H)− (ES−)

Workup

  1. temperaturewarmed to RT
  2. stirringstirred for a further 45 min
  3. temperatureThe suspension was cooled to 0° C.
  4. temperatureThe reaction mixture was warmed to RT
  5. stirringstirred for 2 hr
  6. extractionthe mixture was extracted with ethyl acetate
  7. extractionThe ethyl acetate extract
  8. washwas washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo
  11. customThe residue was purified by flash column chromatography (SiO2, 0-10% ethyl acetate in isohexane, gradient elution)

Sources & evidence

ORD record
ord-30898da2486e4ae3b80ecc4986bddbdd
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

Loading…