Methanol → HCID 55303309, compound

Temperature

-78 °C

(R)-Methyl 3-(methoxymethoxy)-2-methylpropanoate (7, 5.00 g, 0.0308 mol) was is dissolved in methanol (50 mL, 1 mol). The solution was then cooled to −78° C. Sodium methoxide (5.26 g, 0.0925 mol), was added gradually (in very small portions) followed by water (1.11 mL, 0.0616 mol) at −78° C. The reaction mixture was then stirred at 23° C. for 12 hours. An additional portion of NaOMe (95%, 1.0 g) was added to the reaction mixture followed by H2O (0.8 mL). The reaction mixture was allowed to stir at 23° C. for 4 hours. All the solvents were removed under vacuum, and before quenched with concentrated HCl to pH ˜5. Excess of solvents were removed under vacuum. The residue was extracted with DCM (50×3 mL). The combined organic layers were treated with water, brine and dried over Na2SO4. Removal of solvent gave a liquid product (4.37 g, 96%). 1H NMR (CHLOROFORM-d) δ: 4.64 (s, 2H), 3.69-3.82 (m, 1H), 3.56-3.68 (m, 1H), 3.37 (s, 3H), 2.80 (m, 1H), 1.23 (d, J=7.3 Hz, 3H).

1. stirringto stir at 23° C. for 4 hours
2. customAll the solvents were removed under vacuum
3. custombefore quenched with concentrated HCl to pH ˜5
4. customExcess of solvents were removed under vacuum
5. extractionThe residue was extracted with DCM (50×3 mL)
6. additionThe combined organic layers were treated with water, brine
7. dry with materialdried over Na2SO4
8. customRemoval of solvent

ORD record

ord-4c3b0d673d1249d187106c8a0d893033

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349849B2