Boron trifluoride etherate → HCID 89964136, compound

HRID 1846209Notes

Reaction equation

HRID 1846209 reaction equation
[N:1]([C:4]1([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1)=[N+]=[N-].FC(F)(F)C1C=CC(C2(O)C3C(=CC=CC=3)OCC2)=CC=1.[Si](N=[N+]=[N-])(C)(C)C.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1>[F:23][C:20]([F:21])([F:22])[C:17]1[CH:16]=[CH:15][C:14]([C:4]2([NH2:1])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7][CH2:6][CH2:5]2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 78378AzidotrimethylsilaneHCID 89964615HCID 89964615, compoundHCID 89964638HCID 89964638, compound

Product 1

HCID 89964136HCID 89964136, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-azido-4-(4-(trifluoromethyl)phenyl)chroman. To a solution of 4-(4-(trifluoromethyl)phenyl)chroman-4-ol (112 mg, 0.381 mmol) in toluene (4 mL), was added an ice bath and TMS azide (0.101 mL, 0.761 mmol). After 5 min., the solution was treated with BF3.OEt2 (0.048 mL, 0.381 mmol) dropwise. The solution turned from clear to light yellow during the addition. After 20 min, the reaction was quenched with MeOH (2 mL) and diluted with EtOAc (20 mL). The organic solution was washed with water (2×10 mL) and the organic layer concentrated in vacuo to give the title compound as a light yellow oil. MS (ESI pos. ion) m/z: 277.0 (M−N3). 1H NMR (CDCl3) δ: 7.57-7.65 (m, J=8.3 Hz, 2H), 7.41-7.52 (m, J=8.2 Hz, 2H), 7.26-7.33 (m, 1H), 6.81-7.03 (m, 3H), 4.30-4.44 (m, 1H), 4.21-4.30 (m, 1H), 2.23-2.34 (m, 1H), 2.12-2.23 (m, 1H).

Workup

  1. additionlight yellow during the addition
  2. waitAfter 20 min
  3. customthe reaction was quenched with MeOH (2 mL)
  4. additiondiluted with EtOAc (20 mL)
  5. washThe organic solution was washed with water (2×10 mL)
  6. concentrationthe organic layer concentrated in vacuo

Sources & evidence

ORD record
ord-1b40201ce4854a25a3cdedd34a93c9a3
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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