Diethyl Ether → HCID 19027129, compound

HRID 1033095Notes

Reaction equation

C[Si](C)(C)[C:3]1[S:4][CH:5]=[CH:6][N:7]=1.[Li]CC[CH2:13][CH3:14].[CH:15]1[CH:16]=[CH:17][C:18]2[C:19](=[CH:21][CH:22]=[CH:23][C:24]=2[OH:25])[CH:20]=1.[C:26]([O-:29])(O)=[O:27].[Na+].C[CH2:32][O:33]CC>>[S:4]1[C:5]([C:24]2([OH:25])[C:18]3[C:19](=[CH:20][C:15]([O:33][CH3:32])=[CH:16][CH:17]=3)[CH2:21][CH:22]([C:26]([O:29][CH2:13][CH3:14])=[O:27])[CH2:23]2)=[CH:6][N:7]=[CH:3]1

Participants

Reactant 5

HCID 3283Diethyl Ether2×

HCID 70051-Naphthol

HCID 516892Sodium Bicarbonate

HCID 5884532-Trimethylsilylthiazole

HCID 178418339Butyllithium

Product 1

HCID 19027129HCID 19027129, compound

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-trimethylsilylthiazole (2.2 g, 13.9 mmoL) (J. Org. Chem., 1988, 53, 1748) in Et2O (12 mL) was added at -78° C., dropwise a solution of n-BuLi in hexanes (2.45m, 5.68 mL) and the solution was stirred for 30 min. A solution of keto ester from Naphthol 5, Step 3, (2.0 g, 8.05 mmoL) in Et2O (5 mL) was then added dropwise and the reaction was stirred at -78° C. for 1 hr. and warmed to r.t. A saturated NaHCO3 solution was added and the mixture was extracted with Et2O (2×), washed with H2O, dried over MgSO4, filtered and evaporated. The crude compound was purified by flash chromatography on silica gel eluting with hexanes: EtOAc (7:3) to afford directly the title alcohol as an oil.

Workup

temperatureand warmed to r.t
extractionthe mixture was extracted with Et2O (2×)
washwashed with H2O
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customThe crude compound was purified by flash chromatography on silica gel eluting with hexanes: EtOAc (7:3)

Sources & evidence

ORD record: ord-b5c9482ddbcb41dea91886f13c28a4d1
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05308852

Reaction notes

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