Hydrochloric Acid → HCID 57523556, compound

HRID 1879086Notes

Reaction equation

HRID 1879086 reaction equation
[CH3:1][Si:2]([CH3:17])([CH3:16])[C:3]#[C:4][C:5]1([CH3:15])[CH2:14][CH2:13][C:8]2(OCC[O:9]2)[CH2:7][CH2:6]1.Cl>CC(C)=O.[Cl-].[Na+].O>[CH3:15][C:5]1([C:4]#[C:3][Si:2]([CH3:16])([CH3:1])[CH3:17])[CH2:14][CH2:13][C:8](=[O:9])[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57523555HCID 57523555, compound

Product 1

HCID 57523556HCID 57523556, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 6 (2.1 g, 8.3 mmol) in acetone (25 mL) was added 10% aqueous HCl solution (15 mL). The solution was cloudy. Thus, to the cloudy solution, was acetone dropwise (total 12 mL) until the solution was clear. The clear solution was stirred at room temperature for 5 h. The mixture was diluted with brine (250 mL). The aqueous mixture was extracted with methylene chloride/ether (1:2, 200 mL×3). The extract was washed with saturated aqueous bicarbonate solution (2×100 mL) and brine (100 mL×1), dried over MgSO4, and filtered. The filtrate was evaporated in vacuo to give 7 as a crystalline solid (1.7 g, 98%): 1H NMR (CDCl3) δ 2.75, 2.29, 2.04, 1.65 (each 2H, m), 1.32 (3H, s), 0.17 (9H, s); 13C NMR (CDCl3) δ 211.8, 110.8, 86.9, 39.2, 38.8, 32.9, 28.8, 0.4.

Workup

  1. extractionThe aqueous mixture was extracted with methylene chloride/ether (1:2, 200 mL×3)
  2. washThe extract was washed with saturated aqueous bicarbonate solution (2×100 mL) and brine (100 mL×1)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-6541bea864534bf89a8048c0ff6a0f42
Source dataset
uspto-grants-2012_11
Patent number
US08314137B2

Reaction notes

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