Hydrochloric Acid → HCID 16732378, compound

HRID 1160571Notes

Reaction equation

HRID 1160571 reaction equation
Cl.C(#N)C.C([Si]([O:12][C@@H:13]([C@@H:28]([CH3:31])[CH:29]=[CH2:30])/[C:14](/[CH3:27])=[CH:15]/[CH2:16][O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)(C)C)(C)(C)C>[Cl-].[Na+].O>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][CH2:16]/[CH:15]=[C:14](\[CH3:27])/[C@@H:13]([OH:12])[C@@H:28]([CH3:31])[CH:29]=[CH2:30])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 66938059HCID 66938059, compound

Product 1

HCID 16732378HCID 16732378, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

1N hydrochloric acid (100 ml) was added to an acetonitrile (300 ml) solution of tert-butyl({(1S,2E)-4-[(4-methoxybenzyl)oxy]-2-methyl-1-[(1S)-1-methylprop-2-en-1-yl]but-2-en-1-yl}oxy)dimethylsilane (41.8 g, 107 mmol). After the reaction solution was stirred at room temperature for ten and a half hours, it was poured into brine and extracted with ethyl acetate. After the organic layer was washed with brine, it was dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=4:1→3:1→2:1) and was obtained title compound (26.8 g) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with brine, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationAfter the drying agent was filtered off
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (Kanto Chemical, commercial name Silica gel 60N, granular, neutral, 0.040 mm-0.100 mm; n-heptane:ethyl acetate=4:1→3:1→2:1)

Sources & evidence

ORD record
ord-d676b614cd0c44299e281fc6bccb618e
Source dataset
uspto-grants-2010_10
Patent number
US07816401B2

Reaction notes

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