Hydrochloric Acid → HCID 22882495, compound

HRID 863269Notes

Reaction equation

HRID 863269 reaction equation
[O:1]([Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])S(C(F)(F)F)(=O)=O.[Br:19][CH2:20][C@H:21]([CH3:25])[CH2:22][CH2:23]O.N1C(C)=CC=CC=1C.Cl>C(Cl)Cl>[CH:10]([Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[O:1][CH2:23][CH2:22][C@@H:21]([CH3:25])[CH2:20][Br:19])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 14680532HCID 14680532, compound

Product 1

HCID 22882495HCID 22882495, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

15.4 ml of triisopropylsilyl triflate are added to a solution of 8.7 g of (R)-4-bromo-3-methylbutan-1-ol in 320 ml of methylene chloride at 0° C., and 6.6 ml of 2,6-lutidine are then added in the course of 30 min. The reaction mixture is subsequently poured onto 100 ml of ice-water and the aqueous phase is acidified by addition of 2N hydrochloric acid (pH 3). It is extracted with methylene chloride and the organic phase is washed with a 5% sodium bicarbonate solution and saturated sodium chloride solution and dried over sodium sulfate. After purification of the crude product by FC over 200 g of silica gel (mobile phase J), the title compound is obtained: Rf (J)=0.48.

Workup

  1. extractionIt is extracted with methylene chloride
  2. washthe organic phase is washed with a 5% sodium bicarbonate solution and saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customAfter purification of the crude product by FC over 200 g of silica gel (mobile phase J)

Sources & evidence

ORD record
ord-721540f4c86945ceb4ddaff8aeba780f
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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