Tetrabutylammonium Fluoride → (R)-2-Hydroxymethyl-8-methoxy-chroman

HRID 47949Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][C@@H:10]([CH2:13][O:14][Si](C(C)(C)C)(C)C)[CH2:9][CH2:8]2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[O:11][C@@H:10]([CH2:13][OH:14])[CH2:9][CH2:8]2

Participants

Conditions

Temperature: 22 °C

Procedure

To a solution of tert-butyl(dimethyl)silyl [(2R)-8-methoxy-3,4-dihydro-2H-chromen-2-yl]methyl ether (4.50 g, 14.6 mmol) in tetrahydrofuran (150 mL) at 0° C. is added excess tetrabutylammonium fluoride (1.0 M in tetrahydrofuran) and the reaction mixture is allowed to stir at 22° C. for 30 min. The solvent is removed in vacuo and the residue is purified by flash column chromatography (silica, ethyl acetate:hexanes 1:1) to give 2.49 g (88%, 40% ee) of [(2R)-8-methoxy-3,4-dihydro-2H-chromen-2-yl]methanol as a white crystalline solid.

Workup

customThe solvent is removed in vacuo
customthe residue is purified by flash column chromatography (silica, ethyl acetate:hexanes 1:1)

Sources & evidence

ORD record: ord-e8a203b13e884966932cf2606d0b2889
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06700001B2

Reaction notes

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