Imidazole → HCID 11120848, compound

HRID 1700950Notes

Reaction equation

HRID 1700950 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[CH2:14]([O:21][CH2:22][CH2:23][CH2:24][C@H:25]([CH3:28])[CH2:26][OH:27])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH2:14]([O:21][CH2:22][CH2:23][CH2:24][C@H:25]([CH3:28])[CH2:26][O:27][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11593688(S)-5-Benzyloxy-2-methyl-pentan-1-ol

Product 1

HCID 11120848HCID 11120848, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Imidazole (1.230 g, 18.06 mmol, 2.6 equiv) and tert-butyl-dimethylsilyl chloride (1.230 g, 9.03 mmol, 1.3 equiv) are added to a solution of (S)-5-benzyloxy-2-methyl-pentan-1-ol- 4 (1.447 g, 6.95 mmol) in dimethyl formamide (5.5 ml). The mixture is stirred for 1 h at 40° C. Purification of the reaction mixture by flash column chromatography (pentane/diethyl ether 20:1) affords (s)-1-benzyloxy-5-(tert-butyldimethylsilyloxy)-4-methyl-pentane 5 (1.985 g, 89%) as a colouriess oil (the reaction mixture is poured directly without aqueous workup onto a flash chromatography column which is pre-wetted with the eluent). 13C-NMR (100 MHz, CDCl3): δ=138.7; 128.3; 127.5; 127.4; 72.8; 70.8; 68.2; 35.6; 29.6; 27.2; 25.9; 18.3; 16.6; −5.4.

Workup

  1. customPurification of the reaction mixture by flash column chromatography (pentane/diethyl ether 20:1)

Sources & evidence

ORD record
ord-b62f7da643d8453cacc532f168c5157b
Source dataset
uspto-grants-2002_02
Patent number
US06350878B1

Reaction notes

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