Thiazole → 8-(1,3-Thiazol-2-yl)-1,4-dioxaspiro[4.5]decan-8-ol

HRID 1896833Notes

Reaction equation

[Li]CCCC.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[O:11]1[C:15]2([CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]2)[O:14][CH2:13][CH2:12]1>C1COCC1>[S:6]1[CH:10]=[CH:9][N:8]=[C:7]1[C:18]1([OH:21])[CH2:19][CH2:20][C:15]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:16][CH2:17]1

Participants

Conditions

Temperature: -78 °C

Procedure

n-BuLi (2.5 M in hexanes, 26 mL, 65 mmol) was dropped slowly into a solution of thiazole (5.0 g, 59 mmol) in THF (50 mL) at −78° C. in 10 min. The reaction was stirred for additional 20 min. at −78° C. A solution of 1,4-dioxa-spiro[4.5]decan-8-one (9.36 g, 60 mmol) in THF (20 mL) was slowly dropped into the reaction. After addition, the reaction was stirred for additional 2 hours at −78° C. The reaction was then quenched with water solution and warmed to room temperature. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give yellow solid, which was then purified by silica gel column on a CombiFlash system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as white solid.

Workup

additionAfter addition
stirringthe reaction was stirred for additional 2 hours at −78° C
customThe reaction was then quenched with water solution
temperaturewarmed to room temperature
customThe solvent was removed in vacuo
customthe residue was partitioned between ethyl acetate and water
washThe organic layer was washed with brine
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customto give yellow solid, which
customwas then purified by silica gel column on a CombiFlash system

Sources & evidence

ORD record: ord-8b7342353b524b849116fb3b39de186b
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518969B2

Reaction notes

Loading…