p-Toluenesulfonic acid → HCID 14804719, compound

HRID 2108351Notes

Reaction equation

HRID 2108351 reaction equation
C[C:2]([OH:13])([C:9]([O:11][CH3:12])=[O:10])C1C=CC=CC=1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23](S(O)(=O)=O)=[CH:22][CH:21]=1>C(Cl)Cl>[CH3:12][O:11][C:9](=[O:10])[C@@H:2]([O:13][CH:19]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[CH2:30][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 578110(R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester

Product 1

HCID 14804719HCID 14804719, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of L-phenyl lactic acid methyl ester (20.0 g, 111 mmol) in CH2Cl2 (300 mL) was treated with dihydropyran (9.32 g, 111 mmol) and p-toluenesulphonic acid (56 mg) and stirred at room temperature for 20 minutes. The reaction is quenched with 1 N NaOH and then washed with water, brine and dried over Na2SO4. The solution is filtered and the solvent removed under vacuum to give 28 grams of the THP protected alcohol as an oil. This was used without further purification.

Workup

  1. customThe reaction is quenched with 1 N NaOH
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution is filtered
  5. customthe solvent removed under vacuum
  6. customto give 28 grams of the THP
  7. customThis was used without further purification

Sources & evidence

ORD record
ord-2ee832dfbbc24ce4ba724a84c4d17be5
Source dataset
uspto-grants-2009_04
Patent number
US07514430B2

Reaction notes

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