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 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. addition4H2O (32 g, 16 eq.) was introduced at 0° C. portionwise
3. temperaturethe resulting mixture was warmed to room temperature
4. stirringstirred overnight
5. extractionthe separated aqueous phase was extracted with EtOAc
6. dry with materialThe combined organic phase was dried over over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatography (50% to 100% EtOAc-hexanes)

ORD record

ord-12966f28c07e4417ab9fd5ae5eb7ee77

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07314936B2