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 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-c6b198b4f7cb4136b65dc0c5565e0b56

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691814B2