Hydrochloric Acid → HCID 58388115, compound

HRID 1879098Notes

Reaction equation

HRID 1879098 reaction equation
[CH2:1]([C:8]1([C:18]#[C:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH2:17][CH2:16][C:11]2(OCC[O:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CC(C)=O.[Cl-].[Na+].O>[CH2:1]([C:8]1([C:18]#[C:19][Si:20]([CH3:22])([CH3:21])[CH3:23])[CH2:17][CH2:16][C:11](=[O:12])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58388188HCID 58388188, compound

Product 1

HCID 58388115HCID 58388115, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A sample of 29 (243.1 mg, 0.74 mmol) was dissolved in acetone (2.89 mL) to give a translucent, yellow solution. To the solution was added a solution of 10% aqueous hydrochloric acid solution (1.15 mL) and the reaction mixture was stirred at room temperature for 5 hours. The mixture was then diluted with brine (25 mL) and the aqueous layer was extracted with methylene chloride/ethyl ether (1:2, 3×20 mL). The organic layers were combined and washed with saturated aqueous sodium bicarbonate solution (2×20 mL) and brine (1×20 mL), then dried over magnesium sulfate, filtered, and concentrated in vacuo to give the crude 30 as pale yellow crystals (195 mg). The crystals were combined with the crude product of a previous reaction (62.5 mg) and were purified by flash column chromatography [hexanes-ethyl acetate (5:1)] to give 30 as white crystals (197.1 mg, 0.69 mmol, 74%). Note, an impure fraction was collected and saved for future purification. 1H NMR (CDCl3) δ 7.31-7.24 (5H, m), 2.81 (2H, s), 2.74 (2H, td, J=6, 14.5 Hz), 2.30 (2H, dt, J=2, 15 Hz), 2.00 (2H, dt, J=3, 14 Hz), 1.68 (2H, dt, J=4, 13.5 Hz), 0.17 (9H, s); 13C NMR (CDCl3) δ 211.7, 137.1, 130.8, 128.0, 126.9, 109.0, 47.6, 38.6, 38.0, 37.2, 0.29. MS (ESI+) m/z 285.1 [M+H]+, HRMS (ESI+) calcd for C18H24OSi+H 285.1675. found 285.1661.

Workup

  1. customto give a translucent, yellow solution
  2. extractionthe aqueous layer was extracted with methylene chloride/ethyl ether (1:2, 3×20 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (2×20 mL) and brine (1×20 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-177926db8e9b490b9b2ca54b58283aaa
Source dataset
uspto-grants-2012_11
Patent number
US08314137B2

Reaction notes

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