Tetrahydrofuran → 1,4-Dioxaspiro[4.5]decan-8-ylmethanol

To a solution of 8-methyene-1,4-dioxa-spiro[4.5]decane (2.0 g, 13 mmol, 1.0 eq.) in THF (10 mL) at 0° C. was added dropwise 9-BBN (0.5 M in THF, 104 mL, 4.0 eq.) and the resulting mixture was stirred for 15 min and then warmed to room temperature and stirred overnight. Then NaBO4−.4H2O (32 g, 16 eq.) was introduced at 0° C. portionwise and the resulting mixture was warmed to room temperature and stirred overnight, diluted with hexanes (30 mL) and the separated aqueous phase was extracted with EtOAc. The combined organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (50% to 100% EtOAc-hexanes) to give (1,4-dioxa-spiro[4.5]dec-8-yl)-methanol (1.5 g, 67%).

1. stirringstirred overnight
2. temperaturethe resulting mixture was warmed to room temperature
3. stirringstirred overnight
4. extractionthe separated aqueous phase was extracted with EtOAc
5. dry with materialThe combined organic phase was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by silica gel chromatography (50% to 100% EtOAc-hexanes)

ORD record

ord-6f9bccb4f13345118ef0b55dba7f938c

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07868002B2