Imidazole → HCID 86751134, compound

HRID 2256270Notes

Reaction equation

HRID 2256270 reaction equation
O1CC[O:3][CH:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:7]=1[CH:16](O)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].N1C=CN=C1.[C:28]([Si:32](Cl)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:31])([CH3:30])[CH3:29].CN(C=[O:50])C>CCOCC>[Si:32]([O:50][CH:17]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:16][C:7]1[CH:8]=[C:9]([O:14][CH3:15])[C:10]([O:12][CH3:13])=[CH:11][C:6]=1[CH:2]=[O:3])([C:28]([CH3:31])([CH3:30])[CH3:29])([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 54536495HCID 54536495, compound

Product 1

HCID 86751134HCID 86751134, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of (±)-1-(1,3-dioxolanyl)-2-(1-hydroxy)hexyl-4,5-dimethoxybenzene (Compound 32, 2.2 g, 7.09 mmol), imidazole (0.97 g, 14.19 mmol) and t-butylchlorodiphenylsilane (2.8 mL, 10.64 mmol) in DMF (14 mL) was stirred at 23° C. for 72, hours. The reaction was diluted with Et2O and washed with 1N HCl, H2O and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. Flash column chromatography (silica gel, 5:1 hex/EtOAc) gave 3.52 g (99%) of the title compound wherein absence of the acetal blocking group to give the free aldehyde function was unexpected.

Workup

  1. washwashed with 1N HCl, H2O and brine
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3e97b807c6447c985aed7acc4939308
Source dataset
uspto-grants-1997_08
Patent number
US05654329

Reaction notes

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