Boron trifluoride etherate → HCID 15754137, compound

HRID 1461652Notes

Reaction equation

HRID 1461652 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:14])[C:11]=1[O:12][CH3:13])[C:5](O)([CH3:7])[CH3:6].C[Si]([N:19]=[N+]=[N-])(C)C.B(F)(F)F.CCOCC.[BH4-].[Na+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.O.C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:14])[C:11]=1[O:12][CH3:13])[C:5]([NH2:19])([CH3:7])[CH3:6]

Participants

8

Reactant 4

HCID 8000Boron trifluoride etherateHCID 78378AzidotrimethylsilaneHCID 4311764Sodium borohydrideHCID 53743448HCID 53743448, compound

Product 1

HCID 15754137HCID 15754137, compoundYield 63.6%

Reagents, catalysts & solvents 3

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 241BenzeneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A benzene solution of 23.6 g (0.1 mol) of 3,5-dichloro-4-methoxy-α,α-dimethylbenzyl alcohol and 13.9 g (0.12 mol) of trimethylsilyl azide were cooled with ice water, and 17.1 g (0.12 mol) of boron trifluoride ethyl etherate was dropwise added thereto at a temperature not higher than 20° C. under stirring. After completion of the dropwise addition, the mixture was stirred for one hour as it was and further at room temperature for 4 hours. The reaction solution was poured into ice water, and the organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and with water. To this benzene solution, 5.1 g (0.01 mol) of n-hexadecyl tri-n-butylphosphonium bromide was added, and an aqueous solution of 32.4 g (0.9 mol) of sodium borohydride was dropwise added thereto at 80° C. in three times. The reaction solution was poured into water. The organic layer was washed with water and then subjected to liquid separation by an addition of concentrated hydrochloric acid. The aqueous layer was alkalified with sodium hydroxide and then extracted with diethyl ether. The ether solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 14.9 g of the desired compound.

Workup

  1. additionwas dropwise added
  2. additionAfter completion of the dropwise addition
  3. stirringthe mixture was stirred for one hour as it
  4. washthe organic layer was washed with a saturated sodium hydrogencarbonate aqueous solution and with water
  5. customat 80° C.
  6. washThe organic layer was washed with water
  7. customsubjected to liquid separation by an addition of concentrated hydrochloric acid
  8. extractionextracted with diethyl ether
  9. dry with materialThe ether solution was dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e7776fae1aea4dceae1e007e7e9aa7d2
Source dataset
uspto-grants-1991_12
Patent number
US05076834

Reaction notes

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