HCID 12859260, compound → HCID 69311580, compound

Participants

Reaction Steps

A solution of (3S)-3-isopropyl-1,3-dihydro-isobenzofuran-1-ol (2.0 g, 11.2 mmol) in THF (20 mL) was heated under an atmosphere of nitrogen at reflux. To this solution was added slowly a solution of isopropyl magnesium chloride (39.3 mmol) in THF (ca. 20 ml). This solution had been prepared from the commercial solution (19.6 ml 2N solution in ether), from which the solvent had been removed in vacuum, and where the residue was made up with THF to a volume of 20 ml). After the addition of the Grignard reagent was completed, the mixture was stirred for another 30 minutes, and then allowed to cool to ambient temperature. To the mixture was then added a 10% solution of ammonium chloride (ca. 30 ml). The aqueous layer was removed, and re-extracted with TBME (ca. 20 ml). From the combined organic layers the solvent was removed, and the residue was redissolved in TBME (ca. 50 ml). After washing with water and brine, the organic layer was dried (Na2SO4). Removal of the solvent left the product as an oil, 2.2 g (88%). There was only one isomer present by 13C-NMR, which turned out to be the (S,S)-diol. 1H/13C-NMR (CDCl3, HSQC/HMBC) δ/δ 0.783 (d, J=6.7 Hz)/20.02 (CH3); 1.065 (d, J=6.5 Hz)/18.99 (CH3); 2.02 (m)/35.29 (CHMe2); 4.60 (d, J=7.6 Hz)/76.51 (CH(OH)); 2.38 br s (OH); 7.20-7.26 (m)/126.75 (Ar ortho-CH); 7.33-7.39 (m)/127.55 (Ar meta-CH); 141.41 (Ar ipso-C).

Provenance & Evidence