Dimethyl Sulfoxide → HCID 17989289, compound

HRID 1869412Notes

Reaction equation

HRID 1869412 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 while being cooled slightly 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. additionThe reaction mixture is mixed
  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-ce294b009c90483f8185355418ad7eb0
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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