Imidazole → HCID 20284854, compound

HRID 127562Notes

Reaction equation

HRID 127562 reaction equation
N1C=CN=C1.[CH2:6]1[CH2:18][O:17][C:8]([CH3:16])([CH2:9][CH2:10][CH2:11][CH:12]([CH3:15])[CH2:13][OH:14])[O:7]1.[Si:19](Cl)([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[O:14]([CH2:13][CH:12]([CH3:15])[CH2:11][CH2:10][CH2:9][C:8]1([O:7][CH2:6][CH2:18][O:17]1)[CH3:16])[Si:19]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 14078297HCID 14078297, compound

Product 1

HCID 20284854HCID 20284854, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Imidazole (26.5 g) is added to a solution of 6,6-ethylenedioxy-2-methyl-heptanol (33.35 g) in dimethylformamide (50 ml). A solution of t-butyldiphenylsilyl chloride (52.2 g) in dimethylformamide (200 ml) is added dropwise to the reaction mixture and allowed to stir for 3 hours at room temperature. The reaction mixture is extracted with hexane (3×300 ml) and the combined extract is washed with brine and dried (Na2SO4). The solvent is removed in vacuo to give 1-t-butyldiphenylsiloxy-6,6-ethylenedioxy-2-methyl-heptane (75.35 g, 99.6%); nmr (CDCl3,δ), 0.91 (d, 3H, CH3CH), 1.03 [s, (CH3)3C], ##STR43## 3.47 (d, CHCH2O), 3.88 (s, OCH2CH2O), 7.2-7.8 (m, 10 H, 2φ).

Workup

  1. extractionThe reaction mixture is extracted with hexane (3×300 ml)
  2. extractionthe combined extract
  3. washis washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-2d38db563bbb49dcbaf7d2bf7f20bb89
Source dataset
uspto-grants-1981_03
Patent number
US04256644

Reaction notes

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