Dimethyl Sulfoxide → HCID 17989289, compound

HRID 1443228Notes

Reaction equation

HRID 1443228 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. The reaction mixture is mixed with 81 ml of saturated ammonium chloride solution with slight cooling, and it is stirred vigorously. After being extracted twice 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, which resulted from another batch (15.27 g). 15.46 g (72.9%, from 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. stirringis stirred vigorously
  3. extractionAfter being extracted twice with diethyl ether
  4. additionthe combined organic phases are treated as usual
  5. customis chromatographed on silica gel (mobile solvent: ethyl acetate/hexane) together with the residue, which
  6. customresulted from another batch (15.27 g)

Sources & evidence

ORD record
ord-1ce45cd7e30848d39cc523fc30120b9c
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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