Hydrochloric Acid → 3-methyl-3,4-dihydro-2H-chromen-5-ol

HRID 527588Notes

Reaction equation

O.Cl.[CH3:3][CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:14]COC)[O:6][CH2:5]1>CO.ClCCl>[CH3:3][CH:4]1[CH2:13][C:12]2[C:11]([OH:14])=[CH:10][CH:9]=[CH:8][C:7]=2[O:6][CH2:5]1

Participants

Conditions

Temperature: 60 °C

Procedure

In a 8 ml vial 3-methyl-5-{[(methyloxy)methyl]oxy}-3,4-dihydro-2H-chromene (Intermediate 116, 103.6 mg) was dissolved in methanol (3 ml) to give a colourless solution. A 2M/H2O solution of HCl (0.224 ml, 0.448 mmol) was added. The reaction mixture was shaken at 60° C. After 2 h 30 min, the reaction mixture was diluted with 10 ml of dichloromethane. The phases were separated through a phase separator cartridge. The organic phase was evaporated under vacuum to afford the crude product which was purified via Biotage SP1 (with Cyclohexane/EtOAc as eluents from 1:0 to 5:1 in 10 CV; then 5:1 for 5 CV; then from 5:1 to 3:1 in 5 CV; (10 g SNAP Silica column). The collected fractions afforded the title compound as a white solid (53.0 mg).

Workup

customto give a colourless solution
customThe phases were separated through a phase separator cartridge
customThe organic phase was evaporated under vacuum
customto afford the crude product which
customwas purified via Biotage SP1 (with Cyclohexane/EtOAc as eluents from 1:0 to 5:1 in 10 CV

Sources & evidence

ORD record: ord-3ecea19d296045f0bb4889d3022eefd8
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346790B2

Reaction notes

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