Hydrochloric Acid → 4-[1-Hydroxy-4,5-di(t-butyldimethylsilyloxy)-3-oxohexyl]oxazole

HRID 2231885Notes

Reaction equation

[Si:1]([O:8][CH:9]([CH:13]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH3:14])[C:10](=[O:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li].[Li+].CC([N-]C(C)C)C.[CH:32]([C:34]1[N:35]=[CH:36][O:37][CH:38]=1)=[O:33].Cl>C1COCC1>[OH:33][CH:32]([C:34]1[N:35]=[CH:36][O:37][CH:38]=1)[CH2:11][C:10](=[O:12])[CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:13]([O:15][Si:16]([C:19]([CH3:21])([CH3:20])[CH3:22])([CH3:17])[CH3:18])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3,4-di)t-butyldimethylsilyloxy)pentan-2-one (4, 2.8 g, 8 mmol,) in THF (10 mL) was added to -70° C. solution of litium diisopropylaminde (LDA, 8 mmol) in THF (20 mL). After 10 minutes at -70° C., a solution of 4-formyloxazole (1.0 g, 8 mmol--Preparation 15) in THF (5 mL) was added and the resulting mixture allowed to warm to 0° C. Aqueous HCl was added and the mixture extracted with ether. The organic layer was washed with water and brine, dried over MgSO4, evaporated and the residue purified by medium pressure chromatography (0-50% hexane-ethyl acetate gradient) to yield 4-[1-hydroxy-4,5-di-(t-butyldimethylsilyloxy)-3-oxohexyl]oxazole (5).

Workup

extractionthe mixture extracted with ether
washThe organic layer was washed with water and brine
dry with materialdried over MgSO4
customevaporated
customthe residue purified by medium pressure chromatography (0-50% hexane-ethyl acetate gradient)

Sources & evidence

ORD record: ord-16b9f56400b44c6ea9daddcb49966fc5
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04785012

Reaction notes

Loading…