Imidazole → HCID 59671393, compound

HRID 2406264Notes

Reaction equation

[Si:1]([O:8][CH2:9][C@H:10]1[C@@H:14]([OH:15])[CH:13]=[CH:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)Cl.N1C=CN=C1.[Si:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>>[C:4]([Si:1]([O:8][CH2:9][C@@H:10]1[CH2:11][CH:12]=[CH:13][C@@H:14]1[O:15][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

Reactant 4

HCID 795Imidazole

HCID 6344Dichloromethane2×

HCID 28928tert-Butyldimethylsilyl chloride

HCID 11096387HCID 11096387, compound

Product 1

HCID 59671393HCID 59671393, compoundYield 108.3%

Procedure

In an oven-dried 2 L two-neck flask, cooled under nitrogen, to a solution of (1S,5S)-5-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopent-2-en-1-ol (11) (98.07 g, 0.3864 mol) in methylene chloride (500 mL, 8 mol) was added 1H-imidazole (31.57 g, 0.4637 mol). To the resulting yellow solution was added a solution of tert-butyldimethylsilyl chloride (58.2 g, 0.386 mol) in methylene chloride (300 mL, 5 mol) via addition funnel over ˜30 min. The mixture was stirred mechanically for 18 hours. The reaction was quenched via addition of water (500 mL) and the layers were separated. The organic layer was washed with water (2×500 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford tert-butyl[((1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopent-3-en-1-yl)methoxy]dimethylsilane (143.3 g) as a crude residue that was used without further purification.

Workup

additionvia addition funnel over ˜30 min
customThe reaction was quenched via addition of water (500 mL)
customthe layers were separated
washThe organic layer was washed with water (2×500 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7cbf90b4905e46d99641cca6d39423ff
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809356B2

Reaction notes

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