Ammonium Chloride → HCID 86691336, compound

HRID 881997Notes

Reaction equation

HRID 881997 reaction equation
[Li+].[Cl-].FC(F)(F)S(O[C:9]([CH:11]([CH2:16][OH:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[CH2:10])(=O)=O.[Si:20]([CH2:24][Mg]Cl)([CH3:23])([CH3:22])[CH3:21].[NH4+].[Cl-]>CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][CH:13]([CH3:15])[CH2:12][CH:11]([C:9]([CH2:21][Si:20]([CH3:24])([CH3:23])[CH3:22])=[CH2:10])[CH2:16][OH:17]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 56933723HCID 56933723, compoundHCID 178418680HCID 178418680, compound

Product 1

HCID 86691336HCID 86691336, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

LiCl (7.00 mg, 0.159 mmol) and Pd(PPh3)4 (2.30 mg, 0.002 mmol) were added to anhydrous Et2O (1 mL), and then the resulting solution was cooled to 0° C. A solution obtained by dissolving 3-(hydroxymethyl)-5-methylhex-1-ene-2-yl trifluoromethanesulfonate (11 mg, 0.0398 mmol) in anhydrous Et2O (1 mL) was slowly added thereto and the resulting solution was stirred for 10 min. TMSCH2MgCl (0.119 mL, 0.119 mmol, 1.0 M/Et2O solution) was slowly added thereto, the resulting solution was stirred for 1 hr, and then a saturated NH4Cl aqueous solution (1 mL) was added thereto to complete the reaction. The temperature was increased to normal temperature, extraction was performed by using ethyl acetate (3×3 mL), distillation was performed under reduced pressure, and then column chromatography was used to obtain 8.03 mg (yield 94%) of the title compound.

Workup

  1. customA solution obtained
  2. additionwas slowly added
  3. stirringthe resulting solution was stirred for 1 hr
  4. customthe reaction
  5. temperatureThe temperature was increased to normal temperature, extraction
  6. distillationethyl acetate (3×3 mL), distillation

Sources & evidence

ORD record
ord-eb2d883f4f1c4a6f9129a9e0c82f906f
Source dataset
uspto-grants-2015_03
Patent number
US08993766B2

Reaction notes

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