Dimethyl Sulfoxide → HCID 17989289, compound

HRID 1444496Notes

Reaction equation

HRID 1444496 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:18])([CH3:17])[CH2:9][CH:10]([OH:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][C:3]=1[O:19][CH3:20].CS(C)=O.C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl>[CH2:14]([O:13][C:11](=[O:12])[C:10](=[O:16])[CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:19][CH3:20])[CH:4]=1)([CH3:18])[CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 17989149HCID 17989149, compound

Product 1

HCID 17989289HCID 17989289, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.15 g (20.45 mmol) of ethyl 4-(4-chloro-3-methoxyphenyl)-2-hydroxy-4-methyl-pentanoate is dissolved in 213 ml of dichloromethane and mixed with 71 ml of dimethyl sulfoxide. After 10.3 g (102.23 mmol) of triethylamine is added, the batch is mixed in portions with 8.1 g (51.12 mmol) of SO3/pyridine complex and then stirred overnight at room temperature. While being cooled slightly, the reaction mixture is mixed with 81 ml of saturated ammonium chloride solution and vigorously stirred. After 2× extraction with diethyl ether, the combined organic phases are treated as usual. The residue that remains after the solvent is spun off is chromatographed on silica gel (mobile solvent ethyl acetate/hexane) together with the residue that results from another batch (15.27 g). 15.46 g (72.9%, from the two batches) of the desired compound is isolated.

Workup

  1. additionthe batch is mixed in portions with 8.1 g (51.12 mmol) of SO3/pyridine complex
  2. temperatureWhile being cooled slightly
  3. stirringvigorously stirred
  4. extractionAfter 2× extraction with diethyl ether
  5. additionthe combined organic phases are treated as usual
  6. customis chromatographed on silica gel (mobile solvent ethyl acetate/hexane) together with the residue
  7. customthat results from another batch (15.27 g)

Sources & evidence

ORD record
ord-ffb1a22c03dd4472b57f3aa05889d0f3
Source dataset
uspto-grants-2010_02
Patent number
US07662821B2

Reaction notes

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