Dimethyl Sulfoxide → HCID 59161024, compound

HRID 1873559Notes

Reaction equation

HRID 1873559 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:28][CH2:29][CH2:30][O:31][CH:32]1[CH2:37][CH2:36][CH:35]([CH2:38][OH:39])[CH2:34][CH2:33]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl.C(OCC)(=O)C>[Si:11]([O:28][CH2:29][CH2:30][O:31][CH:32]1[CH2:37][CH2:36][CH:35]([CH:38]=[O:39])[CH2:34][CH2:33]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 59160998HCID 59160998, compound

Product 1

HCID 59161024HCID 59161024, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

553.7 mg (4.36 mmol) of oxalyl chloride are dissolved in 25 ml of dichloromethane and cooled to −78° C. 681.6 mg (8.72 mmol) of dimethyl sulfoxide are added slowly. A solution of 1.20 g (2.91 mmol) of the compound from Example 4A in 10 ml of dichloromethane is then added dropwise. The mixture is stirred at −78° C. for 1 h. 2.0 ml (14.54 mmol) of triethylamine are then added, and the mixture is allowed to warm to RT over a period of 1 h. The mixture is then added to 20 ml of a 1:1 mixture of saturated aqueous sodium bicarbonate solution and ethyl acetate. After separation of the phases the aqueous phase is extracted two more times with in each case 10 ml of ethyl acetate. The combined organic phases are freed from the solvent on a rotary evaporator. The residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 20:1→5:1).

Workup

  1. temperatureto warm to RT over a period of 1 h
  2. customAfter separation of the phases the aqueous phase
  3. extractionis extracted two more times with in each case 10 ml of ethyl acetate
  4. customThe combined organic phases are freed from the solvent on a rotary evaporator
  5. customThe residue is purified chromatographically on silica gel 60 (mobile phase: gradient cyclohexane/ethyl acetate 20:1→5:1)

Sources & evidence

ORD record
ord-8e77fdc7c75f4e9a8a610dc4057559b1
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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