Dimethylformamide → 6-((S)-2-Hydroxybutoxy)isochromen-1-one

HRID 69490Notes

Reaction equation

HRID 69490 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH:6]=[CH:5]2.[O:13]1[C@@H:15]([CH2:16][CH3:17])[CH2:14]1.[F-].[Cs+].CN(C=O)C>O>[OH:13][C@@H:15]([CH2:16][CH3:17])[CH2:14][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25953Cesium fluorideHCID 10898629(2S)-2-EthyloxiraneHCID 668796996-Hydroxyisochromen-1-one

Product 1

HCID 668791856-((S)-2-Hydroxybutoxy)isochromen-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 6-Hydroxy-isochromen-1-one (405 mg), (S)-(−)-1,2-epoxybutane (361 mg), cesium fluoride (1.1 g) and DMF (5 mL) was stirred for 4 h at 130° C. After adding water it was extracted with dichloromethane, dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC. In this way the product was obtained with molecular weight 234.25 (C13H1404); MS (ESI): 235 (M+H+).

Workup

  1. extractionwas extracted with dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC
  5. customIn this way the product was obtained with molecular weight 234.25 (C13H1404)

Sources & evidence

ORD record
ord-f1bdf2c6f30a4f709d03ca79a17f77db
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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