Hydrochloric Acid → HCID 19927578, compound

HRID 466641Notes

Reaction equation

HRID 466641 reaction equation
[CH3:1]N(C)P(=O)(N(C)C)N(C)C.[C:12]1(Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl.[CH2:20]1[CH2:24][O:23][CH2:22][CH2:21]1>CCOCC>[CH3:1][C:17]([CH3:12])=[CH:16][CH2:15][CH2:14][CH2:13][CH2:22][CH2:21][CH2:20][CH2:24][OH:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7961BromobenzeneHCID 8028Tetrahydrofuran2×HCID 12679Hexamethylphosphoramide

Product 1

HCID 19927578HCID 19927578, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 55.0 mL (~52 mmol) of 0.95M Grignard reagent prepared in Example 3, Part A in THF and 15.0 mL of hexamethylphosphoric triamide (HMPA) at 0° C. was treated dropwise with 1.95 g (13. 1 mmol) of phenyl bromide in 8 mL of THF over 10 minutes. After the addition the reaction was allowed to warm to room temperature and stir for 3.5 hours, at which point the reaction was diluted with ether and quenched with 100 mL (100 mmol) of 1M HCl solution. The organic layer was washed two times with NH4Cl solution, dried over MgSO4 and evaporated to provide a pale yellow oil. The oil was purified by flash chromatography performed on 200 g of silica gel eluted with 1:4 ethyl acetate/hexanes to provide 3.50 g of oil and hexanol. The hexanol was removed by distillation under reduced pressure (BP 75° C., ~20 mm Hg) to leave 1.50 g (67%) of title compound in the form of a colorless oil. This material contains ~2% of the Sn2' product, which could not be separated.

Workup

  1. additionAfter the addition the reaction
  2. washThe organic layer was washed two times with NH4Cl solution
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customto provide a pale yellow oil
  6. customThe oil was purified by flash chromatography
  7. washeluted with 1:4 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-11a5adec1bda45f5947cf96ebaa8b073
Source dataset
uspto-grants-1992_10
Patent number
US05157027

Reaction notes

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