Methanol → HCID 21950260, compound

HRID 2415524Notes

Reaction equation

HRID 2415524 reaction equation
[CH:1]([C:4]1([CH:10]([OH:14])[CH2:11][CH2:12][CH3:13])SCCCS1)([CH3:3])[CH3:2].C[OH:16]>C(#N)C>[OH:14][CH:10]([CH2:11][CH2:12][CH3:13])[C:4](=[O:16])[CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 14569688HCID 14569688, compound

Product 1

HCID 21950260HCID 21950260, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (101) (5.0 g, 21.4 mmol) in acetonitrile (270 mL) was added under vigorous stirring a solution of Hg(ClO4)2 in methanol (30 mL). The resulting mixture was stirred at room temperature for 2 h. After filtration, the filtrate was carefully concentrated under reduced pressure without heating. Purification of the residue using silica gel flash column chromatography (10% ethyl acetate/hexane) provided 2.8 g (91%) of the title compound as colorless liquid. 1H NMR (CDCl3, 400 MHz): δ 0.91 (t, J=7.2 Hz, 3H), 1.09 (d, J=7.2 Hz, 3H), 1.10 (d, J=7.2 Hz, 3H), 1.35-1.46 (m, 4H), 1.75 (m, 1H), 2.80 (m, 1H), 3.45 (d, J=5.2 Hz, 1H), 4.29 (m, 1H).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was carefully concentrated under reduced pressure
  3. temperaturewithout heating
  4. customPurification of the residue

Sources & evidence

ORD record
ord-219726b6bde64bce8b27bd1f4e9db823
Source dataset
uspto-grants-2004_11
Patent number
US06818787B2

Reaction notes

Loading…