Sodium Perborate → 3-Methoxy-2-(methoxymethyl)propan-1-ol

To a solution of the 3-methoxy-2-methoxymethy-1-propene (3.5 g, 30 mmol, 1.0 eq.) in THF (10 mL) at 0° C. was added BH3.THF (1M in THF, 18 mL, 0.6 eq.) and the resulting mixture was stirred for 40 min. The reaction was quenched with water followed by sodium perborate (10.6 g, 2.3 eq.), warmed to room temperature, stirred overnight, diluted with CH2Cl2 and filtered through celite. The filtrate was diluted with brine and the separated aqueous layer was extracted with CH2Cl2. The combined extracts were dried over Na2SO4 and filtered. The filtrate was didstilled at atmospheric pressure to give light yellow liquid residue. Fractional distillation of the residue at 40 milliTorr gave 3-methoxy-2-methoxymethypropan-1-ol (1.93 g, 48%). b.p.=90-110° C.

1. customThe reaction was quenched with water
2. stirringstirred overnight
3. filtrationfiltered through celite
4. additionThe filtrate was diluted with brine
5. extractionthe separated aqueous layer was extracted with CH2Cl2
6. dry with materialThe combined extracts were dried over Na2SO4
7. filtrationfiltered
8. customto give light yellow liquid residue
9. distillationFractional distillation of the residue at 40 milliTorr

ORD record

ord-fc6ddebf109e4d8a9fe64272a83b3dc4

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07314936B2