p-Toluenesulfonic acid monohydrate → HCID 67099623, compound

HRID 2078346Notes

Reaction equation

HRID 2078346 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][C:10](OCC)([O:14]CC)[O:11][CH2:12][CH3:13])[C:3]=1[C:20]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.O.CC1C=CC(S(O)(=O)=O)=CC=1>CCO.O.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[C:9][C:10]([O:11][CH2:12][CH3:13])=[O:14])[C:3]=1[C:20]1([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

6

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67100193ethyl 4-(2-chloro-6-(3,3,3-triethoxyprop-1-ynyl)phenyl)-tetrahydro-2H-pyran-4-carboxylate

Product 1

HCID 67099623HCID 67099623, compoundYield 59.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 4-(2-chloro-6-(3,3,3-triethoxyprop-1-ynyl)phenyl)-tetrahydro-2H-pyran-4-carboxylate (2.42 g, 5.51 mmol) in 50 mL EtOH and 10 mL water was treated with 4-methylbenzenesulfonic acid hydrate (0.105 g, 0.551 mmol). The mixture was stirred at room temperature for 2 hours. The mixture was diluted with 100 mL EtOAc, washed with 20 mL saturated NaHCO3, dried over anhydrous Na2SO4 and concentrated. The concentrate was purified by column chromatography (20% EtOAc/hexane) to give 1.19 g pale yellow solid. MS m/e: (M+H)+ 365.

Workup

  1. washwashed with 20 mL saturated NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe concentrate was purified by column chromatography (20% EtOAc/hexane)

Sources & evidence

ORD record
ord-00aa6a8cb11a4683b311ccdabd2c0544
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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