p-Toluenesulfonic acid monohydrate → HCID 86709437, compound

HRID 1848411Notes

Reaction equation

HRID 1848411 reaction equation
[CH3:1][C:2]1[C:10]([C@H:11]2[CH2:13][O:12]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:14].[OH2:15].[C:16]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:15][CH2:13][C@@H:11]([C:10]1[C:2]([CH3:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[C:6](=[O:14])[O:5][CH2:4]2)[O:12][CH3:16]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59568665(S)-4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one

Product 1

HCID 86709437HCID 86709437, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (S)-4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one (2.00 g, 10.5 mmol) in MeOH (20 mL) was added p-toluenesulfonic acid monohydrate (0.100 g, 0.526 mmol). After heating at 80° C. for 48 h, the reaction mixture was cooled to RT and then concentrated. The crude product was purified by column chromatography eluting with 0-45% EtOAc/Hexane. LC-MS (IE, m/z): 223.2 (M+1)+.

Workup

  1. temperaturethe reaction mixture was cooled to RT
  2. concentrationconcentrated
  3. customThe crude product was purified by column chromatography
  4. washeluting with 0-45% EtOAc/Hexane

Sources & evidence

ORD record
ord-624096ef5dc144e3ab17c58f16f8af4f
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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