Imidazole → HCID 10991787, compound

HRID 1720232Notes

Reaction equation

HRID 1720232 reaction equation
[OH:1][CH2:2][C@H:3]1[O:8][C:6](=[O:7])[CH:5]=[CH:4]1.CC1(C)O[C@@H]([C@@H](O)[C@H](O)[C@@H]2OC(C)(C)OC2)CO1.N1C=CN=C1.[C:32]([Si:36](Cl)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([CH3:35])([CH3:34])[CH3:33]>CN(C=O)C>[Si:36]([O:1][CH2:2][C@H:3]1[O:8][C:6](=[O:7])[CH:5]=[CH:4]1)([C:32]([CH3:35])([CH3:34])[CH3:33])([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 960111,2:5,6-Di-O-isopropylidene-D-mannitolHCID 10176122(S)-(-)-5-Hydroxymethyl-2(5H)-furanone

Product 1

HCID 10991787HCID 10991787, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-5-hydroxy-2-penten-4-olide [3.2 g, 28.07 mmol; prepared from 1,2:5,6-di-O-isopropylidene-D-mannitol (Aldrich) in a 3-step sequence described by Hafele and Jager in Liebigs Ann. Chem. 1987, 85-87], in dry DMF (50 ml), at 0° C., was added imidazole (2.95 g, 42.1 mmol), followed by tert-butylchlorodiphenylsilane (7.95 ml, 30.9 mmol). The cooling bath was removed and the reaction mixture was stirred at room temperature for a period of 1 h. Then, the solvent was evaporated and the residue was purified on a silica gel column using hexane/EtOAc (7:3 v/v) as the eluent. The appropriate fractions were evaporated and gave 9.0 g (91%) of MSC-006. 13C-NMR (CDCl3)δ: 19.40, 26.88, 63.53, 83.40, 122.89, 128.05, 130.20, 132.68, 132.95, 135.71, 135.76, 154.20. (The carbonyl carbon was not detected).

Workup

  1. customThe cooling bath was removed
  2. customThen, the solvent was evaporated
  3. customthe residue was purified on a silica gel column
  4. customThe appropriate fractions were evaporated

Sources & evidence

ORD record
ord-2b10f623aace45fd9904081fe58569f9
Source dataset
uspto-grants-1996_04
Patent number
US05506215

Reaction notes

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