Hydrochloric Acid → HCID 66849286, compound

HRID 929455Notes

Reaction equation

HRID 929455 reaction equation
Cl.[I:2][C:3]1([CH2:6][C@H:7]([CH2:16][O:17][Si](C)(C)C(C)(C)C)[O:8][Si](C)(C)C(C)(C)C)[CH2:5][CH2:4]1>C1COCC1>[I:2][C:3]1([CH2:6][C@@H:7]([OH:8])[CH2:16][OH:17])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66849204HCID 66849204, compound

Product 1

HCID 66849286HCID 66849286, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous HCl solution (0.3 mL, 1N) was added to a solution of (R)-5-((1-iodocyclopropyl)methyl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane (step E, 281 mg, 0.598 mmol) in THF (2 mL) at 0° C. The mixture was slowly warmed at room temperature and stirred for 24 hours. The reaction was quenched by addition of aqueous NaHCO3 solution and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure to provide (R)-3-(1-iodocyclopropyl)propane-1,2-diol (0.598 mmol), which was used in the next step with no further purification.

Workup

  1. customThe reaction was quenched by addition of aqueous NaHCO3 solution
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e48de7cc8844eb6ba95fa031b5487ab
Source dataset
uspto-grants-2016_03
Patent number
US09296686B2

Reaction notes

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