Imidazole → tert-Butyl(chloro)phenylsilane

HRID 2206343Notes

Reaction equation

HRID 2206343 reaction equation
OCC=C(CCC=C(CCC=C(C)C)C)C.N1C=CN=C1.CN(C)C=O.[Si:27]([Cl:44])([C:40]([CH3:43])([CH3:42])[CH3:41])(C1C=CC=CC=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[C:40]([SiH:27]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[Cl:44])([CH3:43])([CH3:41])[CH3:42]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3327a Farnesol2×HCID 6228DimethylformamideHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 71357688tert-Butyl(chloro)phenylsilaneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesis was carried out with farnesol as a starting material. A protective group was bonded to the hydroxy group of farnesol using imidazole, anhydrous dimethylformamide, anhydrous dichloromethane, and tert-butyldiphenylsilyl chloride (TBDPS) to obtain a TBDPS-protected form (fi) (yield: 99%). Next, this compound was reacted with m-chloroperbenzoic acid in an anhydrous dichloromethane solvent to obtain an epoxy form (fii) (yield: 29%). The epoxy was subjected to periodic acid oxidation using orthoperiodic acid in a mixed solvent of ether and tetrahydrofuran to obtain an aldehyde form (fiii) (yield: 73%). A Grignard reagent was prepared from ethyl iodide and magnesium in an anhydrous ether solvent and then reacted with the aldehyde to form an alcohol form (fiv) (yield: 80%). The TBDPS group in the compound (fiv) was removed using tetrabutylammonium fluoride in an anhydrous tetrahydrofuran solvent to form a diol form (fv) (yield: 93%).

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-206107fb9d6d4a128cb37acb4627545b
Source dataset
uspto-grants-2016_06
Patent number
US09371342B2

Reaction notes

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